Total synthesis of kendomycin featuring intramolecular dötz benzannulation

Kyosuke Tanaka; Masahito Watanabe; Kodai Ishibashi; Hiroshi Matsuyama; Yoko Saikawa; Masaya Nakata

doi:10.1021/ol100229f

Total synthesis of kendomycin featuring intramolecular dötz benzannulation

Kyosuke Tanaka, Masahito Watanabe, Kodai Ishibashi, Hiroshi Matsuyama, Yoko Saikawa, Masaya Nakata

Department of Applied Chemistry

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

29 Citations (Scopus)

Abstract

One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

Original language	English
Pages (from-to)	1700-1703
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	8
DOIs	https://doi.org/10.1021/ol100229f
Publication status	Published - 2010 Apr 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol100229f

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abstract = "One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular D{\"o}tz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.",

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AU - Tanaka, Kyosuke

AU - Watanabe, Masahito

AU - Ishibashi, Kodai

AU - Matsuyama, Hiroshi

AU - Saikawa, Yoko

AU - Nakata, Masaya

PY - 2010/4/16

Y1 - 2010/4/16

N2 - One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

AB - One-step formation of the ansa-skeleton realized the synthesis of kendomycin, an ansa-type quinone methide. The Fischer carbene complex derived from the ansa-chain portion was subjected to the intramolecular Dötz benzannulation to afford the desired oxametacyclophane with exclusive regioselectivity. Subsequent Claisen rearrangement, ortho oxidation of the resulting phenol derivative, and mild transformation from p-quinone to p-quinone methide on a silica gel plate furnished kendomycin.

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JO - Organic Letters

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Total synthesis of kendomycin featuring intramolecular dötz benzannulation

Abstract

ASJC Scopus subject areas

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