Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

Akinobu Nakahara; Misaki Kanbe; Masahisa Nakada

doi:10.1016/j.tetlet.2012.01.058

Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

Akinobu Nakahara, Misaki Kanbe, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

6 Citations (Scopus)

Abstract

This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product.

Original language	English
Pages (from-to)	1518-1522
Number of pages	5
Journal	Tetrahedron Letters
Volume	53
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2012.01.058
Publication status	Published - 2012 Mar 21

Keywords

Bucidarasin
Cascade reaction
Diels-Alder reaction
Michael reaction
Stereoselective reaction
Transannular reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2012.01.058

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title = "Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity",

abstract = "This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product.",

keywords = "Bucidarasin, Cascade reaction, Diels-Alder reaction, Michael reaction, Stereoselective reaction, Transannular reaction",

author = "Akinobu Nakahara and Misaki Kanbe and Masahisa Nakada",

note = "Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research on Innovative Areas (No. 21106009) and the Global COE program “Center for Practical Chemical Wisdom” by MEXT.",

year = "2012",

month = mar,

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doi = "10.1016/j.tetlet.2012.01.058",

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journal = "Tetrahedron Letters",

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T1 - Synthetic studies on (+)-bucidarasin C

T2 - Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

AU - Nakahara, Akinobu

AU - Kanbe, Misaki

AU - Nakada, Masahisa

N1 - Funding Information: This work was financially supported in part by a Waseda University Grant for Special Research Projects, a Grant-in-Aid for Scientific Research on Innovative Areas (No. 21106009) and the Global COE program “Center for Practical Chemical Wisdom” by MEXT.

PY - 2012/3/21

Y1 - 2012/3/21

N2 - This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product.

AB - This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product.

KW - Bucidarasin

KW - Cascade reaction

KW - Diels-Alder reaction

KW - Michael reaction

KW - Stereoselective reaction

KW - Transannular reaction

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DO - 10.1016/j.tetlet.2012.01.058

M3 - Article

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SN - 0040-4039

VL - 53

SP - 1518

EP - 1522

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Synthetic studies on (+)-bucidarasin C: Two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

Abstract

Keywords

ASJC Scopus subject areas

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