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 › peer-review

20 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

Access to Document

10.1016/j.tetlet.2007.09.039

Fingerprint Dive into the research topics of 'The first total synthesis and structural determination of (+)-BE-52440A'. Together they form a unique fingerprint.

Cite this

@article{f884a6b7c8884ebba8efe1e1e3318096,

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",

month = nov,

day = "5",

doi = "10.1016/j.tetlet.2007.09.039",

language = "English",

volume = "48",

pages = "8018--8021",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "45",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=35148820598&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=35148820598&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2007.09.039

DO - 10.1016/j.tetlet.2007.09.039

M3 - Article

AN - SCOPUS:35148820598

VL - 48

SP - 8018

EP - 8021

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 45

ER -