A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor

Hiyoshizo Kotsuki, Isao Kadota, Masamitsu Ochi

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81 Citations (Scopus)

Abstract

We describe here a full account of a highly concise and enantiospecific synthesis of (+)-exo-brevicomin (7), (5R,6S)-(-)-6-acetoxy-5-hexadecanolide (11), and L-factor (16) originating from D- or L-tartrates as chiral sources. The synthesis employs an efficient carbon-carbon bond-forming reaction of inflates with copper(I)-catalyzed Grignard reagents and, as a consequence, tosyl-triflate derivatives 6 and 15 were found to be a versatile intermediate. This methodology completed the synthetic scheme involving a five-step sequence from 1 to 7, a 10-step sequence from 2 to 11, and a seven-step sequence from 12 to 16. The results present a new rapid means to derive optically active natural products from readily available chiral building blocks.

Original languageEnglish
Pages (from-to)4417-4422
Number of pages6
JournalJournal of Organic Chemistry
Volume55
Issue number14
Publication statusPublished - 1990
Externally publishedYes

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Tartrates
Copper
Carbon
Biological Products
Derivatives
brevicomin
6-acetoxy-5-hexadecanolide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor",
abstract = "We describe here a full account of a highly concise and enantiospecific synthesis of (+)-exo-brevicomin (7), (5R,6S)-(-)-6-acetoxy-5-hexadecanolide (11), and L-factor (16) originating from D- or L-tartrates as chiral sources. The synthesis employs an efficient carbon-carbon bond-forming reaction of inflates with copper(I)-catalyzed Grignard reagents and, as a consequence, tosyl-triflate derivatives 6 and 15 were found to be a versatile intermediate. This methodology completed the synthetic scheme involving a five-step sequence from 1 to 7, a 10-step sequence from 2 to 11, and a seven-step sequence from 12 to 16. The results present a new rapid means to derive optically active natural products from readily available chiral building blocks.",
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T1 - A novel carbon-carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents. A new concise and enantiospecific synthesis of (+)-exo-brevicomin, (5R,6S)-(-)-6-acetoxy-5-hexadecanolide, and L-factor

AU - Kotsuki, Hiyoshizo

AU - Kadota, Isao

AU - Ochi, Masamitsu

PY - 1990

Y1 - 1990

N2 - We describe here a full account of a highly concise and enantiospecific synthesis of (+)-exo-brevicomin (7), (5R,6S)-(-)-6-acetoxy-5-hexadecanolide (11), and L-factor (16) originating from D- or L-tartrates as chiral sources. The synthesis employs an efficient carbon-carbon bond-forming reaction of inflates with copper(I)-catalyzed Grignard reagents and, as a consequence, tosyl-triflate derivatives 6 and 15 were found to be a versatile intermediate. This methodology completed the synthetic scheme involving a five-step sequence from 1 to 7, a 10-step sequence from 2 to 11, and a seven-step sequence from 12 to 16. The results present a new rapid means to derive optically active natural products from readily available chiral building blocks.

AB - We describe here a full account of a highly concise and enantiospecific synthesis of (+)-exo-brevicomin (7), (5R,6S)-(-)-6-acetoxy-5-hexadecanolide (11), and L-factor (16) originating from D- or L-tartrates as chiral sources. The synthesis employs an efficient carbon-carbon bond-forming reaction of inflates with copper(I)-catalyzed Grignard reagents and, as a consequence, tosyl-triflate derivatives 6 and 15 were found to be a versatile intermediate. This methodology completed the synthetic scheme involving a five-step sequence from 1 to 7, a 10-step sequence from 2 to 11, and a seven-step sequence from 12 to 16. The results present a new rapid means to derive optically active natural products from readily available chiral building blocks.

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