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

School of Science

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

Access to Document

10.1021/ol400157s

Cite this

@article{84647d6efbd74375bf2d3e29b5c4f3e9,

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

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.",

author = "Hiroyoshi Takamura and Kohei Iwamoto and Eiji Nakao and Isao Kadota",

year = "2013",

month = mar,

doi = "10.1021/ol400157s",

language = "English",

volume = "15",

pages = "1108--1111",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Total synthesis of two possible diastereomers of (+)-sarcophytonolide C and its structural elucidation

AU - Takamura, Hiroyoshi

AU - Iwamoto, Kohei

AU - Nakao, Eiji

AU - Kadota, Isao

PY - 2013/3

Y1 - 2013/3

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84874591046&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84874591046&partnerID=8YFLogxK

U2 - 10.1021/ol400157s

DO - 10.1021/ol400157s

M3 - Article

C2 - 23406537

AN - SCOPUS:84874591046

SN - 1523-7060

VL - 15

SP - 1108

EP - 1111

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this