Synthetic study of azaspiracid-1: Synthesis of the EFGHI-ring fragment

Masato Oikawa; Tomoko Uehara; Taizo Iwayama; Makoto Sasaki

doi:10.1021/ol0613766

Synthetic study of azaspiracid-1: Synthesis of the EFGHI-ring fragment

Masato Oikawa, Tomoko Uehara, Taizo Iwayama, Makoto Sasaki

LIF - Molecular and Chemical Life Science

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

16 Citations (Scopus)

Abstract

Here, we report a synthesis of the lower half C₂₁-C₄₀ fragment of the shellfish toxin, azaspiracid-1. The C₂₈-C ₄₀ fragment was synthesized by a coupling between the C ₂₈-C₃₅ epoxide and the C₃₆-C₄₀ dithioacetal anion, followed by the HI-ring spiroaminal formation. An aldehyde corresponding to the C₂₈-C₄₀ fragment was then coupled with the C₂₁-C₂₇ allylic stannane by using InCl ₃. Finally, the FG-ring was constructed by HF-pyridine to accomplish the synthesis of the suitably protected C₂₁-C₄₀ fragment.

Original language	English
Pages (from-to)	3943-3946
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	18
DOIs	https://doi.org/10.1021/ol0613766
Publication status	Published - 2006 Aug 31

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthetic study of azaspiracid-1: Synthesis of the EFGHI-ring fragment",

abstract = "Here, we report a synthesis of the lower half C21-C40 fragment of the shellfish toxin, azaspiracid-1. The C28-C 40 fragment was synthesized by a coupling between the C 28-C35 epoxide and the C36-C40 dithioacetal anion, followed by the HI-ring spiroaminal formation. An aldehyde corresponding to the C28-C40 fragment was then coupled with the C21-C27 allylic stannane by using InCl 3. Finally, the FG-ring was constructed by HF-pyridine to accomplish the synthesis of the suitably protected C21-C40 fragment.",

author = "Masato Oikawa and Tomoko Uehara and Taizo Iwayama and Makoto Sasaki",

year = "2006",

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journal = "Organic Letters",

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T1 - Synthetic study of azaspiracid-1

T2 - Synthesis of the EFGHI-ring fragment

AU - Oikawa, Masato

AU - Uehara, Tomoko

AU - Iwayama, Taizo

AU - Sasaki, Makoto

PY - 2006/8/31

Y1 - 2006/8/31

N2 - Here, we report a synthesis of the lower half C21-C40 fragment of the shellfish toxin, azaspiracid-1. The C28-C 40 fragment was synthesized by a coupling between the C 28-C35 epoxide and the C36-C40 dithioacetal anion, followed by the HI-ring spiroaminal formation. An aldehyde corresponding to the C28-C40 fragment was then coupled with the C21-C27 allylic stannane by using InCl 3. Finally, the FG-ring was constructed by HF-pyridine to accomplish the synthesis of the suitably protected C21-C40 fragment.

AB - Here, we report a synthesis of the lower half C21-C40 fragment of the shellfish toxin, azaspiracid-1. The C28-C 40 fragment was synthesized by a coupling between the C 28-C35 epoxide and the C36-C40 dithioacetal anion, followed by the HI-ring spiroaminal formation. An aldehyde corresponding to the C28-C40 fragment was then coupled with the C21-C27 allylic stannane by using InCl 3. Finally, the FG-ring was constructed by HF-pyridine to accomplish the synthesis of the suitably protected C21-C40 fragment.

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