The synthesis of naturally occurring 4-alkyl- and 4-alkenyl-γ-lactones using the asymmetric reducing agent B-3-pinanyl-9-borabicyclo[3.3.1]nonane

M. Mark Midland, Alfonso Tramontano

Research output: Contribution to journalArticle

58 Citations (Scopus)

Abstract

4-Hydroxy-2-alkynoates of high enantiomeric purity, available from the reduction of the corresponding ketones with B-3-pinanyl-9-BBN, are converted to 4-substituted-γ-lactones found in beetle and deer pheromones.

Original languageEnglish (US)
Pages (from-to)3549-3552
Number of pages4
JournalTetrahedron Letters
Volume21
Issue number37
DOIs
StatePublished - 1980

Fingerprint

Deer
Pheromones
Beetles
Reducing Agents
Lactones
Ketones
nonane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The synthesis of naturally occurring 4-alkyl- and 4-alkenyl-γ-lactones using the asymmetric reducing agent B-3-pinanyl-9-borabicyclo[3.3.1]nonane. / Midland, M. Mark; Tramontano, Alfonso.

In: Tetrahedron Letters, Vol. 21, No. 37, 1980, p. 3549-3552.

Research output: Contribution to journalArticle

@article{859e69785d004e529a23a125890adbad,
title = "The synthesis of naturally occurring 4-alkyl- and 4-alkenyl-γ-lactones using the asymmetric reducing agent B-3-pinanyl-9-borabicyclo[3.3.1]nonane",
abstract = "4-Hydroxy-2-alkynoates of high enantiomeric purity, available from the reduction of the corresponding ketones with B-3-pinanyl-9-BBN, are converted to 4-substituted-γ-lactones found in beetle and deer pheromones.",
author = "Midland, {M. Mark} and Alfonso Tramontano",
year = "1980",
doi = "10.1016/0040-4039(80)80232-2",
language = "English (US)",
volume = "21",
pages = "3549--3552",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "37",

}

TY - JOUR

T1 - The synthesis of naturally occurring 4-alkyl- and 4-alkenyl-γ-lactones using the asymmetric reducing agent B-3-pinanyl-9-borabicyclo[3.3.1]nonane

AU - Midland, M. Mark

AU - Tramontano, Alfonso

PY - 1980

Y1 - 1980

N2 - 4-Hydroxy-2-alkynoates of high enantiomeric purity, available from the reduction of the corresponding ketones with B-3-pinanyl-9-BBN, are converted to 4-substituted-γ-lactones found in beetle and deer pheromones.

AB - 4-Hydroxy-2-alkynoates of high enantiomeric purity, available from the reduction of the corresponding ketones with B-3-pinanyl-9-BBN, are converted to 4-substituted-γ-lactones found in beetle and deer pheromones.

UR - http://www.scopus.com/inward/record.url?scp=0001665661&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001665661&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(80)80232-2

DO - 10.1016/0040-4039(80)80232-2

M3 - Article

AN - SCOPUS:0001665661

VL - 21

SP - 3549

EP - 3552

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 37

ER -