Synthetic studies on fully substituted γ-pyrone-containing natural products: The first total synthesis of onchitriol II

Hirokazu Arimoto; Shigeru Nishiyama; Shosuke Yamamura

doi:10.1016/0040-4039(94)88516-8

Synthetic studies on fully substituted γ-pyrone-containing natural products: The first total synthesis of onchitriol II

Hirokazu Arimoto, Shigeru Nishiyama, Shosuke Yamamura

LIF - Molecular and Chemical Life Science

Keio University

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

18 Citations (Scopus)

Abstract

The first total synthesis of onchitriol II, a cytotoxic metabolite of mollusc Onchidium sp., is described. It employs mild cyclization method [DMSO - (COCl)₂ or Ph₃P - CCl₄] of triketides bearing optically active functional groups to the corresponding γ-pyrones as a key step. Additional synthesis of some diastereoisomers provided a possibility to revise the structure of closely related onchitriol I.

Original language	English
Pages (from-to)	9581-9584
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	51
DOIs	https://doi.org/10.1016/0040-4039(94)88516-8
Publication status	Published - 1994 Dec 19

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abstract = "The first total synthesis of onchitriol II, a cytotoxic metabolite of mollusc Onchidium sp., is described. It employs mild cyclization method [DMSO - (COCl)2 or Ph3P - CCl4] of triketides bearing optically active functional groups to the corresponding γ-pyrones as a key step. Additional synthesis of some diastereoisomers provided a possibility to revise the structure of closely related onchitriol I.",

author = "Hirokazu Arimoto and Shigeru Nishiyama and Shosuke Yamamura",

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AU - Nishiyama, Shigeru

AU - Yamamura, Shosuke

PY - 1994/12/19

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AB - The first total synthesis of onchitriol II, a cytotoxic metabolite of mollusc Onchidium sp., is described. It employs mild cyclization method [DMSO - (COCl)2 or Ph3P - CCl4] of triketides bearing optically active functional groups to the corresponding γ-pyrones as a key step. Additional synthesis of some diastereoisomers provided a possibility to revise the structure of closely related onchitriol I.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Synthetic studies on fully substituted γ-pyrone-containing natural products: The first total synthesis of onchitriol II

Abstract

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