Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (+)-β-eudesmol

Eugene A. Mash; James A. Fryling

doi:10.1021/jo00390a010

Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (+)-β-eudesmol

Eugene A. Mash
, James A. Fryling

Chemistry and Biochemistry

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

29 Scopus citations

Abstract

An enantioselective preparation of (+)-β-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal. The overall yield of (+)-β-eudesmol (75% ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-l(2H)-one is 25% over eight steps.

Original language	English (US)
Pages (from-to)	3000-3003
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	52
Issue number	14
DOIs	https://doi.org/10.1021/jo00390a010
State	Published - Jul 1 1987

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/jo00390a010

Cite this

@article{220bb643f57b4950af586b758689d5a8,

title = "Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (+)-β-eudesmol",

abstract = "An enantioselective preparation of (+)-β-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal. The overall yield of (+)-β-eudesmol (75\% ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-l(2H)-one is 25\% over eight steps.",

author = "Mash, \{Eugene A.\} and Fryling, \{James A.\}",

year = "1987",

month = jul,

day = "1",

doi = "10.1021/jo00390a010",

language = "English (US)",

volume = "52",

pages = "3000--3003",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (+)-β-eudesmol

AU - Mash, Eugene A.

AU - Fryling, James A.

PY - 1987/7/1

Y1 - 1987/7/1

N2 - An enantioselective preparation of (+)-β-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal. The overall yield of (+)-β-eudesmol (75% ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-l(2H)-one is 25% over eight steps.

AB - An enantioselective preparation of (+)-β-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal. The overall yield of (+)-β-eudesmol (75% ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-l(2H)-one is 25% over eight steps.

UR - https://www.scopus.com/pages/publications/0023228868

UR - https://www.scopus.com/pages/publications/0023228868#tab=citedBy

U2 - 10.1021/jo00390a010

DO - 10.1021/jo00390a010

M3 - Article

AN - SCOPUS:0023228868

SN - 0022-3263

VL - 52

SP - 3000

EP - 3003

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (+)-β-eudesmol

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this