Spongistatin Synthetic Studies. Evolution of a Scalable Synthesis for the EF Fragment of (+)-Spongistatin 1 Exploiting a Petasis−Ferrier Union/Rearrangement Tactic

An efficient, stereocontrolled, and scalable second-generation synthesis of (+)-3, an advanced EF subtarget for the total synthesis of (+)-spongistatin 1, has been achieved. Highlights of the strategy include preparation of the F-ring pyran via a Petasis−Ferrier union/rearrangement sequence and inst...

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Veröffentlicht in:	Organic letters 2004-09, Vol.6 (20), p.3637-3640
Hauptverfasser:	Smith, Amos B, Sfouggatakis, Chris, Gotchev, Dimitar B, Shirakami, Shohei, Bauer, David, Zhu, Wenyu, Doughty, Victoria A
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Catalysis Cyclization Indicators and Reagents Macrolides - analysis Macrolides - chemical synthesis Molecular Structure Porifera - chemistry Stereoisomerism
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creator	Smith, Amos B Sfouggatakis, Chris Gotchev, Dimitar B Shirakami, Shohei Bauer, David Zhu, Wenyu Doughty, Victoria A
description	An efficient, stereocontrolled, and scalable second-generation synthesis of (+)-3, an advanced EF subtarget for the total synthesis of (+)-spongistatin 1, has been achieved. Highlights of the strategy include preparation of the F-ring pyran via a Petasis−Ferrier union/rearrangement sequence and installation of the chlorodiene side chain employing a cyanohydrin alkylation. The longest linear sequence, 26 steps, proceeds in 8.3% overall yield.
doi_str_mv	10.1021/ol048418f
format	Article
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subjects	Animals Catalysis Cyclization Indicators and Reagents Macrolides - analysis Macrolides - chemical synthesis Molecular Structure Porifera - chemistry Stereoisomerism
title	Spongistatin Synthetic Studies. Evolution of a Scalable Synthesis for the EF Fragment of (+)-Spongistatin 1 Exploiting a Petasis−Ferrier Union/Rearrangement Tactic
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