The first total synthesis and structural determination of (+)-BE-52440A

Kuniaki Tatsuta; Yoshikazu Suzuki; Tatsuya Toriumi; Yoshiaki Furuya; Seijiro Hosokawa

doi:10.1016/j.tetlet.2007.09.039

The first total synthesis and structural determination of (+)-BE-52440A

Kuniaki Tatsuta, Yoshikazu Suzuki, Tatsuya Toriumi, Yoshiaki Furuya, Seijiro Hosokawa

School of Advanced Science and Engineering

Research output: Contribution to journal › Article

19 Citations (Scopus)

Abstract

The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including S_N2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone.

Original language	English
Pages (from-to)	8018-8021
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2007.09.039
Publication status	Published - 2007 Nov 5

Keywords

BE-52440A
Dimerization
Enantiodivergent synthesis
Tetrasubstituted epoxide
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "The first total synthesis and structural determination of (+)-BE-52440A",

abstract = "The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including SN2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone.",

keywords = "BE-52440A, Dimerization, Enantiodivergent synthesis, Tetrasubstituted epoxide, Total synthesis",

author = "Kuniaki Tatsuta and Yoshikazu Suzuki and Tatsuya Toriumi and Yoshiaki Furuya and Seijiro Hosokawa",

year = "2007",

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journal = "Tetrahedron Letters",

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T1 - The first total synthesis and structural determination of (+)-BE-52440A

AU - Tatsuta, Kuniaki

AU - Suzuki, Yoshikazu

AU - Toriumi, Tatsuya

AU - Furuya, Yoshiaki

AU - Hosokawa, Seijiro

PY - 2007/11/5

Y1 - 2007/11/5

N2 - The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including SN2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone.

AB - The first total synthesis and structural determination of (+)-BE-52440A have been achieved by enantiodivergent synthesis. S-Bridging dimerization including SN2 epoxy-opening reaction of tetrasubstituted epoxide 2 with sodium sulfide has been achieved in excellent yield with high regioselectivity. The structure of (+)-BE-52440A was determined to be the dimer of kalafungin type pyranonaphthoquinone.

KW - BE-52440A

KW - Dimerization

KW - Enantiodivergent synthesis

KW - Tetrasubstituted epoxide

KW - Total synthesis

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DO - 10.1016/j.tetlet.2007.09.039

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EP - 8021

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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