Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model

Troy Lam; Nancy I. Totah

doi:10.1016/j.tetlet.2015.01.026

Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model

Troy Lam, Nancy I. Totah

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

4 Scopus citations

Abstract

The synthesis of a C31-C47 model of spirastrellolide A is reported. Key steps include an iron catalyzed cross coupling reaction to incorporate the linear side chain as a single unit, and the carbonyl ene reaction of an exocyclic enol ether to prepare the 5,6-spiroketal. A trans-ketalization from 5,6- to 6,6-spiroketal frameworks is used to facilitate stereochemical assignment.

Original language	English (US)
Pages (from-to)	3349-3352
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.026
State	Published - May 25 2015

Keywords

Carbonyl ene reaction
Exocyclic enol ether
Iron catalyzed coupling reaction
Spirastrellolide
Spiroketals
trans-Ketalization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.01.026

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title = "Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model",

abstract = "The synthesis of a C31-C47 model of spirastrellolide A is reported. Key steps include an iron catalyzed cross coupling reaction to incorporate the linear side chain as a single unit, and the carbonyl ene reaction of an exocyclic enol ether to prepare the 5,6-spiroketal. A trans-ketalization from 5,6- to 6,6-spiroketal frameworks is used to facilitate stereochemical assignment.",

keywords = "Carbonyl ene reaction, Exocyclic enol ether, Iron catalyzed coupling reaction, Spirastrellolide, Spiroketals, trans-Ketalization",

author = "Troy Lam and Totah, {Nancy I.}",

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T1 - Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model

AU - Lam, Troy

AU - Totah, Nancy I.

PY - 2015/5/25

Y1 - 2015/5/25

N2 - The synthesis of a C31-C47 model of spirastrellolide A is reported. Key steps include an iron catalyzed cross coupling reaction to incorporate the linear side chain as a single unit, and the carbonyl ene reaction of an exocyclic enol ether to prepare the 5,6-spiroketal. A trans-ketalization from 5,6- to 6,6-spiroketal frameworks is used to facilitate stereochemical assignment.

AB - The synthesis of a C31-C47 model of spirastrellolide A is reported. Key steps include an iron catalyzed cross coupling reaction to incorporate the linear side chain as a single unit, and the carbonyl ene reaction of an exocyclic enol ether to prepare the 5,6-spiroketal. A trans-ketalization from 5,6- to 6,6-spiroketal frameworks is used to facilitate stereochemical assignment.

KW - Carbonyl ene reaction

KW - Exocyclic enol ether

KW - Iron catalyzed coupling reaction

KW - Spirastrellolide

KW - Spiroketals

KW - trans-Ketalization

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DO - 10.1016/j.tetlet.2015.01.026

M3 - Article

AN - SCOPUS:84939941267

SN - 0040-4039

VL - 56

SP - 3349

EP - 3352

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Studies toward the synthesis of spirastrellolide A. Preparation of a C31-C47 model

Abstract

Keywords

ASJC Scopus subject areas

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