Marine natural products-XVI. Polyhalogenated acyclic monoterpenes from the red alga plocamium of antarctica

Donald B. Stierle; Richard M. Wing; James J. Sims

doi:10.1016/S0040-4020(01)99499-2

Marine natural products-XVI. Polyhalogenated acyclic monoterpenes from the red alga plocamium of antarctica

Donald B. Stierle
, Richard M. Wing
, James J. Sims

University of California at Riverside

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

Examination of the red alga Plocamium sp. collected near the Antarctic penninsula yielded three new acyclic halogenated monoterpenes (1-3). A structure revision is proposed for a compound previously reported to have structure 1. X-ray diffraction provided the structure of 1 including absolute stereochemistry. The structures of 2 and 3 followed from proton and ¹³C NMR spectral interpretation.

Original language	English
Pages (from-to)	2855-2859
Number of pages	5
Journal	Tetrahedron
Volume	35
Issue number	24
DOIs	https://doi.org/10.1016/S0040-4020(01)99499-2
State	Published - 1979

Funding

After reduction of the data, 679 of the 8$9 unique relkctions collected in an octant out to sin WA= 0.481 were accepted using the criteria of F 2 1.5 cp Attempts to solve the structure by Patterson methods were frustrated by a large number of overlapping peaks, hence, we resorted to a direct methods approach to locating the five halogen atoms.z The solutions and refinement then proceeded routinely to give the structure shown in the @ure. Large anomolous dispersion contributions from the halogen atoms resulted in a weighted residual of 9.9% for the correct con@uratio# as against 10.5% for the enantiomer. The final unweighted residual was 10.7%a nd X was l.85.24 Acknowkdgements-The algal sample was provided by Dr. T. E. DeLaca MSF-OPP-74121391. This work was surmorted bv the National.Science Foundation’CHE74-13938.T he &uker G-9& D18 was supported by the NIH Biomedical Science Grant No. 5-SG5-RRO7010-19an d by the NSF Grant No. MPS75-06138.

Funder number
5-SG5-RRO7010-19an

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

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10.1016/S0040-4020(01)99499-2

Cite this

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title = "Marine natural products-XVI. Polyhalogenated acyclic monoterpenes from the red alga plocamium of antarctica",

abstract = "Examination of the red alga Plocamium sp. collected near the Antarctic penninsula yielded three new acyclic halogenated monoterpenes (1-3). A structure revision is proposed for a compound previously reported to have structure 1. X-ray diffraction provided the structure of 1 including absolute stereochemistry. The structures of 2 and 3 followed from proton and 13C NMR spectral interpretation.",

author = "Stierle, \{Donald B.\} and Wing, \{Richard M.\} and Sims, \{James J.\}",

note = "Funding Information: After reduction of the data, 679 of the 8\$9 unique relkctions collected in an octant out to sin WA= 0.481 were accepted using the criteria of F 2 1.5 cp Attempts to solve the structure by Patterson methods were frustrated by a large number of overlapping peaks, hence, we resorted to a direct methods approach to locating the five halogen atoms.z The solutions and refinement then proceeded routinely to give the structure shown in the @ure. Large anomolous dispersion contributions from the halogen atoms resulted in a weighted residual of 9.9\% for the correct con@uratio\# as against 10.5\% for the enantiomer. The final unweighted residual was 10.7\%a nd X was l.85.24 Acknowkdgements-The algal sample was provided by Dr. T. E. DeLaca MSF-OPP-74121391. This work was surmorted bv the National.Science Foundation{\textquoteright}CHE74-13938.T he \&uker G-9\& D18 was supported by the NIH Biomedical Science Grant No. 5-SG5-RRO7010-19an d by the NSF Grant No. MPS75-06138.",

year = "1979",

doi = "10.1016/S0040-4020(01)99499-2",

language = "English",

volume = "35",

pages = "2855--2859",

journal = "Tetrahedron",

issn = "0040-4020",

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number = "24",

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T1 - Marine natural products-XVI. Polyhalogenated acyclic monoterpenes from the red alga plocamium of antarctica

AU - Stierle, Donald B.

AU - Wing, Richard M.

AU - Sims, James J.

N1 - Funding Information: After reduction of the data, 679 of the 8$9 unique relkctions collected in an octant out to sin WA= 0.481 were accepted using the criteria of F 2 1.5 cp Attempts to solve the structure by Patterson methods were frustrated by a large number of overlapping peaks, hence, we resorted to a direct methods approach to locating the five halogen atoms.z The solutions and refinement then proceeded routinely to give the structure shown in the @ure. Large anomolous dispersion contributions from the halogen atoms resulted in a weighted residual of 9.9% for the correct con@uratio# as against 10.5% for the enantiomer. The final unweighted residual was 10.7%a nd X was l.85.24 Acknowkdgements-The algal sample was provided by Dr. T. E. DeLaca MSF-OPP-74121391. This work was surmorted bv the National.Science Foundation’CHE74-13938.T he &uker G-9& D18 was supported by the NIH Biomedical Science Grant No. 5-SG5-RRO7010-19an d by the NSF Grant No. MPS75-06138.

PY - 1979

Y1 - 1979

N2 - Examination of the red alga Plocamium sp. collected near the Antarctic penninsula yielded three new acyclic halogenated monoterpenes (1-3). A structure revision is proposed for a compound previously reported to have structure 1. X-ray diffraction provided the structure of 1 including absolute stereochemistry. The structures of 2 and 3 followed from proton and 13C NMR spectral interpretation.

AB - Examination of the red alga Plocamium sp. collected near the Antarctic penninsula yielded three new acyclic halogenated monoterpenes (1-3). A structure revision is proposed for a compound previously reported to have structure 1. X-ray diffraction provided the structure of 1 including absolute stereochemistry. The structures of 2 and 3 followed from proton and 13C NMR spectral interpretation.

UR - https://www.scopus.com/pages/publications/0008181862

U2 - 10.1016/S0040-4020(01)99499-2

DO - 10.1016/S0040-4020(01)99499-2

M3 - Article

AN - SCOPUS:0008181862

SN - 0040-4020

VL - 35

SP - 2855

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Marine natural products-XVI. Polyhalogenated acyclic monoterpenes from the red alga plocamium of antarctica

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UN SDGs

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