First synthesis of (±)-halichonadins A-D

Ryohei Fujita; Kaito Ooka; Hiroaki Wasada; Yoshiyasu Ichikawa; Seijiro Hosokawa

doi:10.1039/d4ob00088a

First synthesis of (±)-halichonadins A-D

Ryohei Fujita, Kaito Ooka, Hiroaki Wasada, Yoshiyasu Ichikawa^*, Seijiro Hosokawa^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

Abstract

Described herein is the first total synthesis of a marine isocyanide terpene, (±)-halichonadin C. Our synthetic strategy features nitrile-to-isocyanide interconversion utilizing hypervalent iodine-promoted Hofmann rearrangement. This approach led to successful construction of an isocyanide group at the stereochemically encumbered C-6 position in (±)-halichonadin C. Furthermore, in accord with a scenario we propose for the biosynthesis of halichonadins A-D, (±)-halichonadin C was transformed to halichonadins A and B via the missing link intermediate, halichonadin isocyanate.

Original language	English
Pages (from-to)	1901-1906
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	22
Issue number	9
DOIs	https://doi.org/10.1039/d4ob00088a
Publication status	Published - 2024 Feb 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "First synthesis of (±)-halichonadins A-D",

abstract = "Described herein is the first total synthesis of a marine isocyanide terpene, (±)-halichonadin C. Our synthetic strategy features nitrile-to-isocyanide interconversion utilizing hypervalent iodine-promoted Hofmann rearrangement. This approach led to successful construction of an isocyanide group at the stereochemically encumbered C-6 position in (±)-halichonadin C. Furthermore, in accord with a scenario we propose for the biosynthesis of halichonadins A-D, (±)-halichonadin C was transformed to halichonadins A and B via the missing link intermediate, halichonadin isocyanate.",

author = "Ryohei Fujita and Kaito Ooka and Hiroaki Wasada and Yoshiyasu Ichikawa and Seijiro Hosokawa",

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AU - Fujita, Ryohei

AU - Ooka, Kaito

AU - Wasada, Hiroaki

AU - Ichikawa, Yoshiyasu

AU - Hosokawa, Seijiro

PY - 2024/2/6

Y1 - 2024/2/6

N2 - Described herein is the first total synthesis of a marine isocyanide terpene, (±)-halichonadin C. Our synthetic strategy features nitrile-to-isocyanide interconversion utilizing hypervalent iodine-promoted Hofmann rearrangement. This approach led to successful construction of an isocyanide group at the stereochemically encumbered C-6 position in (±)-halichonadin C. Furthermore, in accord with a scenario we propose for the biosynthesis of halichonadins A-D, (±)-halichonadin C was transformed to halichonadins A and B via the missing link intermediate, halichonadin isocyanate.

AB - Described herein is the first total synthesis of a marine isocyanide terpene, (±)-halichonadin C. Our synthetic strategy features nitrile-to-isocyanide interconversion utilizing hypervalent iodine-promoted Hofmann rearrangement. This approach led to successful construction of an isocyanide group at the stereochemically encumbered C-6 position in (±)-halichonadin C. Furthermore, in accord with a scenario we propose for the biosynthesis of halichonadins A-D, (±)-halichonadin C was transformed to halichonadins A and B via the missing link intermediate, halichonadin isocyanate.

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SN - 1477-0520

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

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ER -

First synthesis of (±)-halichonadins A-D

Abstract

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