Enantioselective total synthesis of convolutamydines B and E

Tomoaki Nakamura; Shin Ichi Shirokawa; Seijiro Hosokawa; Atsuo Nakazaki; Susumu Kobayashi

doi:10.1021/ol052871p

Enantioselective total synthesis of convolutamydines B and E

Tomoaki Nakamura, Shin Ichi Shirokawa, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi^*

^*Corresponding author for this work

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

109 Citations (Scopus)

Abstract

The first enantioselective total synthesis of convolutamydines B and E has been achieved using our vinylogous Mukaiyama aldol reaction. The synthesis features highly diastereoselective vinylogous Mukaiyama aldol reaction with isatin instead of aldehydes to construct a chiral center of convolutamydines. Additionally, the absolute configuration of natural convolutamydine B has been determined as R by its CD spectrum.

Original language	English
Pages (from-to)	677-679
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	4
DOIs	https://doi.org/10.1021/ol052871p
Publication status	Published - 2006 Feb 16
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol052871p

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abstract = "The first enantioselective total synthesis of convolutamydines B and E has been achieved using our vinylogous Mukaiyama aldol reaction. The synthesis features highly diastereoselective vinylogous Mukaiyama aldol reaction with isatin instead of aldehydes to construct a chiral center of convolutamydines. Additionally, the absolute configuration of natural convolutamydine B has been determined as R by its CD spectrum.",

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AU - Hosokawa, Seijiro

AU - Nakazaki, Atsuo

AU - Kobayashi, Susumu

PY - 2006/2/16

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AB - The first enantioselective total synthesis of convolutamydines B and E has been achieved using our vinylogous Mukaiyama aldol reaction. The synthesis features highly diastereoselective vinylogous Mukaiyama aldol reaction with isatin instead of aldehydes to construct a chiral center of convolutamydines. Additionally, the absolute configuration of natural convolutamydine B has been determined as R by its CD spectrum.

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Enantioselective total synthesis of convolutamydines B and E

Abstract

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