Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin

Tohru Oishi, Mitsuru Shoji, Kenji Maeda, Naomi Kumahara, Masahiro Hirama

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

The extensive ring-expansion strategy for the synthesis of oxepene 19, oxocane 23, and oxonene 28, which correspond to the D (E), I and F ring fragments of ciguatoxin (1), respectively, has been established. Chemoenzymatic asymmetric acylation of the meso alcohols using lipase AK provided a simple entry of the enantiomeric building blocks.

Original languageEnglish
Pages (from-to)1165-1167
Number of pages3
JournalSynlett
Volume1996
Issue number12
DOIs
Publication statusPublished - Jan 1 1996

Fingerprint

Oxepins
Ciguatoxins
Acylation
Ethers
Lipase
Alcohols

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin. / Oishi, Tohru; Shoji, Mitsuru; Maeda, Kenji; Kumahara, Naomi; Hirama, Masahiro.

In: Synlett, Vol. 1996, No. 12, 01.01.1996, p. 1165-1167.

Research output: Contribution to journalArticle

Oishi, Tohru ; Shoji, Mitsuru ; Maeda, Kenji ; Kumahara, Naomi ; Hirama, Masahiro. / Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin. In: Synlett. 1996 ; Vol. 1996, No. 12. pp. 1165-1167.
@article{9c7add23d3a44335a48b35119e60be9c,
title = "Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin",
abstract = "The extensive ring-expansion strategy for the synthesis of oxepene 19, oxocane 23, and oxonene 28, which correspond to the D (E), I and F ring fragments of ciguatoxin (1), respectively, has been established. Chemoenzymatic asymmetric acylation of the meso alcohols using lipase AK provided a simple entry of the enantiomeric building blocks.",
author = "Tohru Oishi and Mitsuru Shoji and Kenji Maeda and Naomi Kumahara and Masahiro Hirama",
year = "1996",
month = "1",
day = "1",
doi = "10.1055/s-1996-5729",
language = "English",
volume = "1996",
pages = "1165--1167",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "12",

}

TY - JOUR

T1 - Extensive Ring-Expansion Strategy for the Enantioselective Synthesis of the Medium Ring Ethers, Oxepene, Oxocane, and Oxonene, of Ciguatoxin

AU - Oishi, Tohru

AU - Shoji, Mitsuru

AU - Maeda, Kenji

AU - Kumahara, Naomi

AU - Hirama, Masahiro

PY - 1996/1/1

Y1 - 1996/1/1

N2 - The extensive ring-expansion strategy for the synthesis of oxepene 19, oxocane 23, and oxonene 28, which correspond to the D (E), I and F ring fragments of ciguatoxin (1), respectively, has been established. Chemoenzymatic asymmetric acylation of the meso alcohols using lipase AK provided a simple entry of the enantiomeric building blocks.

AB - The extensive ring-expansion strategy for the synthesis of oxepene 19, oxocane 23, and oxonene 28, which correspond to the D (E), I and F ring fragments of ciguatoxin (1), respectively, has been established. Chemoenzymatic asymmetric acylation of the meso alcohols using lipase AK provided a simple entry of the enantiomeric building blocks.

UR - http://www.scopus.com/inward/record.url?scp=0001828376&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001828376&partnerID=8YFLogxK

U2 - 10.1055/s-1996-5729

DO - 10.1055/s-1996-5729

M3 - Article

AN - SCOPUS:0001828376

VL - 1996

SP - 1165

EP - 1167

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 12

ER -