Stereocontrolled Synthesis of (±)-Grandisol

William R. Bartlett; Javier Read De Alaniz; Janet L. Carlson; Maria P. Dillon; Eric Edstrom; Derek A. Fischer; Adam A. Goldblum; Gregory R. Luedtke; Gregory W. Paneitz; Kendal Ryter; Mark Schulz; Donnie A. Shepard; Christopher Switzer

doi:10.1055/s-0040-1719910

Stereocontrolled Synthesis of (±)-Grandisol

William R. Bartlett
, Javier Read De Alaniz
, Janet L. Carlson
, Maria P. Dillon
, Eric Edstrom
, Derek A. Fischer
, Adam A. Goldblum
, Gregory R. Luedtke
, Gregory W. Paneitz
, Kendal Ryter
, Mark Schulz
, Donnie A. Shepard
, Christopher Switzer

Center for Translational Medicine

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

1 Scopus citations

Abstract

A synthetic approach to grandisol is described. The route to the cyclobutane core relies on an efficient intramolecular [2+2] cycloaddition that establishes the required cis-ring fusion at the adjacent side chains of the cyclobutane ring. Using a new two-step lithium/halide homologation procedure, norgrandisol was efficiently converted into grandisol. This new approach enables the synthesis of grandisol in five steps from commercially available starting material in 22% overall yield.

Original language	English
Pages (from-to)	3209-3214
Number of pages	6
Journal	Synthesis (Germany)
Volume	54
Issue number	14
DOIs	https://doi.org/10.1055/s-0040-1719910
State	Published - Jul 4 2022

Keywords

[2+2] cycloaddition
boll weevil
cyclobutene ring
grandisol
homologation
photocyclization

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10.1055/s-0040-1719910

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title = "Stereocontrolled Synthesis of (±)-Grandisol",

abstract = "A synthetic approach to grandisol is described. The route to the cyclobutane core relies on an efficient intramolecular [2+2] cycloaddition that establishes the required cis-ring fusion at the adjacent side chains of the cyclobutane ring. Using a new two-step lithium/halide homologation procedure, norgrandisol was efficiently converted into grandisol. This new approach enables the synthesis of grandisol in five steps from commercially available starting material in 22\% overall yield.",

keywords = "[2+2] cycloaddition, boll weevil, cyclobutene ring, grandisol, homologation, photocyclization",

author = "Bartlett, \{William R.\} and \{Read De Alaniz\}, Javier and Carlson, \{Janet L.\} and Dillon, \{Maria P.\} and Eric Edstrom and Fischer, \{Derek A.\} and Goldblum, \{Adam A.\} and Luedtke, \{Gregory R.\} and Paneitz, \{Gregory W.\} and Kendal Ryter and Mark Schulz and Shepard, \{Donnie A.\} and Christopher Switzer",

year = "2022",

month = jul,

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doi = "10.1055/s-0040-1719910",

language = "English",

volume = "54",

pages = "3209--3214",

journal = "Synthesis (Germany)",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Stereocontrolled Synthesis of (±)-Grandisol

AU - Bartlett, William R.

AU - Read De Alaniz, Javier

AU - Carlson, Janet L.

AU - Dillon, Maria P.

AU - Edstrom, Eric

AU - Fischer, Derek A.

AU - Goldblum, Adam A.

AU - Luedtke, Gregory R.

AU - Paneitz, Gregory W.

AU - Ryter, Kendal

AU - Schulz, Mark

AU - Shepard, Donnie A.

AU - Switzer, Christopher

PY - 2022/7/4

Y1 - 2022/7/4

N2 - A synthetic approach to grandisol is described. The route to the cyclobutane core relies on an efficient intramolecular [2+2] cycloaddition that establishes the required cis-ring fusion at the adjacent side chains of the cyclobutane ring. Using a new two-step lithium/halide homologation procedure, norgrandisol was efficiently converted into grandisol. This new approach enables the synthesis of grandisol in five steps from commercially available starting material in 22% overall yield.

AB - A synthetic approach to grandisol is described. The route to the cyclobutane core relies on an efficient intramolecular [2+2] cycloaddition that establishes the required cis-ring fusion at the adjacent side chains of the cyclobutane ring. Using a new two-step lithium/halide homologation procedure, norgrandisol was efficiently converted into grandisol. This new approach enables the synthesis of grandisol in five steps from commercially available starting material in 22% overall yield.

KW - [2+2] cycloaddition

KW - boll weevil

KW - cyclobutene ring

KW - grandisol

KW - homologation

KW - photocyclization

UR - https://www.scopus.com/pages/publications/85128864545

U2 - 10.1055/s-0040-1719910

DO - 10.1055/s-0040-1719910

M3 - Article

AN - SCOPUS:85128864545

SN - 0039-7881

VL - 54

SP - 3209

EP - 3214

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 14

ER -

Stereocontrolled Synthesis of (±)-Grandisol

Abstract

Keywords

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