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

21 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",

note = "Funding Information: This work was financially supported by the Consolidated Research Institute for Advanced Science and Medical Care, the Global COE program {\textquoteleft}Center for Practical Chemical Wisdom{\textquoteright}, and Scientific Research on Priority Area {\textquoteleft}Creation of Biologically Functional Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology. ",

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

language = "English",

volume = "48",

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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

N1 - Funding Information: This work was financially supported by the Consolidated Research Institute for Advanced Science and Medical Care, the Global COE program ‘Center for Practical Chemical Wisdom’, and Scientific Research on Priority Area ‘Creation of Biologically Functional Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology.

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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VL - 48

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 45

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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