Mirror image synthesis left ends of ciguatoxin and gambiertoxin 4b

Seijiro Hosokawa, Minoru Isobe

Research output: Contribution to journalArticle

87 Citations (Scopus)

Abstract

Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.

Original languageEnglish
Pages (from-to)37-48
Number of pages12
JournalJournal of Organic Chemistry
Volume64
Issue number1
DOIs
Publication statusPublished - 1999 Jan 8
Externally publishedYes

Fingerprint

Ciguatoxins
Mirrors
Pentoses
Acetylene
Stereochemistry
Cyclization
Derivatives
gambiertoxin (CTX-4B)

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Mirror image synthesis left ends of ciguatoxin and gambiertoxin 4b. / Hosokawa, Seijiro; Isobe, Minoru.

In: Journal of Organic Chemistry, Vol. 64, No. 1, 08.01.1999, p. 37-48.

Research output: Contribution to journalArticle

@article{5fa5749fdbb44047acecb817904b316f,
title = "Mirror image synthesis left ends of ciguatoxin and gambiertoxin 4b",
abstract = "Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.",
author = "Seijiro Hosokawa and Minoru Isobe",
year = "1999",
month = "1",
day = "8",
doi = "10.1021/jo980088n",
language = "English",
volume = "64",
pages = "37--48",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Mirror image synthesis left ends of ciguatoxin and gambiertoxin 4b

AU - Hosokawa, Seijiro

AU - Isobe, Minoru

PY - 1999/1/8

Y1 - 1999/1/8

N2 - Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.

AB - Three compounds related to the AB fragments of ciguatoxin and gambiertoxin 4b and two diastereomers (at the C-2 position) of the ABC fragment of ciguatoxin have been synthesized in enantiomeric form. The stereochemistry of the C-2 position was introduced selectively from the corresponding pentose derivative. Construction of the A ring with its side chain was completed by Nicholas type cyclization of an acetylene bis(cobalthexacarbonyl) complex followed by reductive decomplexation.

UR - http://www.scopus.com/inward/record.url?scp=0033534666&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033534666&partnerID=8YFLogxK

U2 - 10.1021/jo980088n

DO - 10.1021/jo980088n

M3 - Article

VL - 64

SP - 37

EP - 48

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 1

ER -