Total synthesis of (-)-13-oxyingenol and its natural derivative

Takayuki Ohyoshi; Shota Funakubo; Yamato Miyazawa; Keisuke Niida; Ichiro Hayakawa; Hideo Kigoshi

doi:10.1002/anie.201201383

Total synthesis of (-)-13-oxyingenol and its natural derivative

Takayuki Ohyoshi, Shota Funakubo, Yamato Miyazawa, Keisuke Niida, Ichiro Hayakawa, Hideo Kigoshi

School of Engineering

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

38 Citations (Scopus)

Abstract

Ring functionalization: The total synthesis of a natural derivative of (-)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow-Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (-)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.

Original language	English
Pages (from-to)	4972-4975
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	20
DOIs	https://doi.org/10.1002/anie.201201383
Publication status	Published - May 14 2012

Keywords

13-oxyingenol
inside-outside framework
metathesis
sigmatropic rearrangement
terpenoids

ASJC Scopus subject areas

Catalysis
Chemistry(all)

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/anie.201201383

Cite this

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abstract = "Ring functionalization: The total synthesis of a natural derivative of (-)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow-Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (-)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.",

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AU - Ohyoshi, Takayuki

AU - Funakubo, Shota

AU - Miyazawa, Yamato

AU - Niida, Keisuke

AU - Hayakawa, Ichiro

AU - Kigoshi, Hideo

PY - 2012/5/14

Y1 - 2012/5/14

N2 - Ring functionalization: The total synthesis of a natural derivative of (-)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow-Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (-)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.

AB - Ring functionalization: The total synthesis of a natural derivative of (-)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow-Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (-)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.

KW - 13-oxyingenol

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KW - metathesis

KW - sigmatropic rearrangement

KW - terpenoids

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Total synthesis of (-)-13-oxyingenol and its natural derivative

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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