Enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B

Akira Morita; Hiromasa Kiyota; Shigefumi Kuwahara

doi:10.1271/bbb.60253

Enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B

Akira Morita, Hiromasa Kiyota, Shigefumi Kuwahara

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

6 Citations (Scopus)

Abstract

An enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B was accomplished in line with our previously reported synthetic pathway for their (1R,5S)-enantiomer. The use of "EtSCeCl ₂" prepared from EtSLi and CeCl3, instead of previously employed EtSLi itself, for the formation of thiol ester intermediates prevented any undesirable epimerization occurring in the process.

Original language	English
Pages (from-to)	2564-2566
Number of pages	3
Journal	Bioscience, Biotechnology and Biochemistry
Volume	70
Issue number	10
DOIs	https://doi.org/10.1271/bbb.60253
Publication status	Published - 2006
Externally published	Yes

Keywords

Anti-HIV
Enantioselective synthesis
Litseaverticillol
Sesquiterpenoid

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

UN SDGs

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

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10.1271/bbb.60253

Cite this

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title = "Enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B",

abstract = "An enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B was accomplished in line with our previously reported synthetic pathway for their (1R,5S)-enantiomer. The use of {"}EtSCeCl 2{"} prepared from EtSLi and CeCl3, instead of previously employed EtSLi itself, for the formation of thiol ester intermediates prevented any undesirable epimerization occurring in the process.",

keywords = "Anti-HIV, Enantioselective synthesis, Litseaverticillol, Sesquiterpenoid",

author = "Akira Morita and Hiromasa Kiyota and Shigefumi Kuwahara",

note = "Funding Information: This work was financially supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 16380075).",

year = "2006",

doi = "10.1271/bbb.60253",

language = "English",

volume = "70",

pages = "2564--2566",

journal = "Bioscience, Biotechnology and Biochemistry",

issn = "0916-8451",

publisher = "Japan Society for Bioscience Biotechnology and Agrochemistry",

number = "10",

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TY - JOUR

T1 - Enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B

AU - Morita, Akira

AU - Kiyota, Hiromasa

AU - Kuwahara, Shigefumi

N1 - Funding Information: This work was financially supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 16380075).

PY - 2006

Y1 - 2006

N2 - An enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B was accomplished in line with our previously reported synthetic pathway for their (1R,5S)-enantiomer. The use of "EtSCeCl 2" prepared from EtSLi and CeCl3, instead of previously employed EtSLi itself, for the formation of thiol ester intermediates prevented any undesirable epimerization occurring in the process.

AB - An enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B was accomplished in line with our previously reported synthetic pathway for their (1R,5S)-enantiomer. The use of "EtSCeCl 2" prepared from EtSLi and CeCl3, instead of previously employed EtSLi itself, for the formation of thiol ester intermediates prevented any undesirable epimerization occurring in the process.

KW - Anti-HIV

KW - Enantioselective synthesis

KW - Litseaverticillol

KW - Sesquiterpenoid

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DO - 10.1271/bbb.60253

M3 - Article

C2 - 17031060

AN - SCOPUS:33750450522

SN - 0916-8451

VL - 70

SP - 2564

EP - 2566

JO - Bioscience, Biotechnology and Biochemistry

JF - Bioscience, Biotechnology and Biochemistry

IS - 10

ER -

Enantioselective synthesis of the (1S,5R)-enantiomer of litseaverticillols A and B

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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