Total synthesis of two possible diastereomers of (+)-sarcophytonolide C and its structural elucidation

Hiroyoshi Takamura; Kohei Iwamoto; Eiji Nakao; Isao Kadota

doi:10.1021/ol400157s

Total synthesis of two possible diastereomers of (+)-sarcophytonolide C and its structural elucidation

Hiroyoshi Takamura, Kohei Iwamoto, Eiji Nakao, Isao Kadota

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

14 Citations (Scopus)

Abstract

Stereoselective and parallel total syntheses of two possible diastereomers of (+)-sarcophytonolide C have been accomplished. Macrolactonization and transannular ring-closing metathesis (RCM) were the key transformations. Detailed comparisons of their ¹H and ¹³C NMR data and specific rotation with those of the natural product allowed the absolute configuration of (+)-sarcophytonolide C to be determined.

Original language	English
Pages (from-to)	1108-1111
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	5
DOIs	https://doi.org/10.1021/ol400157s
Publication status	Published - Mar 2013

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Stereoselective and parallel total syntheses of two possible diastereomers of (+)-sarcophytonolide C have been accomplished. Macrolactonization and transannular ring-closing metathesis (RCM) were the key transformations. Detailed comparisons of their 1H and 13C NMR data and specific rotation with those of the natural product allowed the absolute configuration of (+)-sarcophytonolide C to be determined.",

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AU - Takamura, Hiroyoshi

AU - Iwamoto, Kohei

AU - Nakao, Eiji

AU - Kadota, Isao

PY - 2013/3

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AB - Stereoselective and parallel total syntheses of two possible diastereomers of (+)-sarcophytonolide C have been accomplished. Macrolactonization and transannular ring-closing metathesis (RCM) were the key transformations. Detailed comparisons of their 1H and 13C NMR data and specific rotation with those of the natural product allowed the absolute configuration of (+)-sarcophytonolide C to be determined.

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Total synthesis of two possible diastereomers of (+)-sarcophytonolide C and its structural elucidation

Abstract

ASJC Scopus subject areas

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