A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde

Hiroaki Okamura, Satoru Kuroda, Satoru Ikegami, Kenji Tomita, Yu ichi Sugimoto, Shin ichi Sakaguchi, Yoshio Ito, Tsutomu Katsuki, Masaru Yamaguchi

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

This paper describes the enantioselective synthesis of key fragments (12, 18, 24, and 35) for the synthesis of aplysiatoxin (1a), a potent cancer promoter, and their convergent assembly to Kishi's aldehyde (2). Since 2 has already been transformed into 1a in a short step, its synthesis constitutes a formal total synthesis of 1a. Synthesis of fragments of aplysiatoxin (1a) and their convergent assembly to the key intermediate, Kishi's aldehyde (2), for the synthesis of 1a are described.

Original languageEnglish
Pages (from-to)10531-10554
Number of pages24
JournalTetrahedron
Volume49
Issue number46
DOIs
Publication statusPublished - 1993

Fingerprint

Aldehydes
Neoplasms
aplysiatoxin

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Okamura, H., Kuroda, S., Ikegami, S., Tomita, K., Sugimoto, Y. I., Sakaguchi, S. I., ... Yamaguchi, M. (1993). A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde. Tetrahedron, 49(46), 10531-10554. https://doi.org/10.1016/S0040-4020(01)81547-7

A formal synthesis of aplysiatoxin : enantioselective synthesis of kishi's aldehyde. / Okamura, Hiroaki; Kuroda, Satoru; Ikegami, Satoru; Tomita, Kenji; Sugimoto, Yu ichi; Sakaguchi, Shin ichi; Ito, Yoshio; Katsuki, Tsutomu; Yamaguchi, Masaru.

In: Tetrahedron, Vol. 49, No. 46, 1993, p. 10531-10554.

Research output: Contribution to journalArticle

Okamura, H, Kuroda, S, Ikegami, S, Tomita, K, Sugimoto, YI, Sakaguchi, SI, Ito, Y, Katsuki, T & Yamaguchi, M 1993, 'A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde', Tetrahedron, vol. 49, no. 46, pp. 10531-10554. https://doi.org/10.1016/S0040-4020(01)81547-7
Okamura H, Kuroda S, Ikegami S, Tomita K, Sugimoto YI, Sakaguchi SI et al. A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde. Tetrahedron. 1993;49(46):10531-10554. https://doi.org/10.1016/S0040-4020(01)81547-7
Okamura, Hiroaki ; Kuroda, Satoru ; Ikegami, Satoru ; Tomita, Kenji ; Sugimoto, Yu ichi ; Sakaguchi, Shin ichi ; Ito, Yoshio ; Katsuki, Tsutomu ; Yamaguchi, Masaru. / A formal synthesis of aplysiatoxin : enantioselective synthesis of kishi's aldehyde. In: Tetrahedron. 1993 ; Vol. 49, No. 46. pp. 10531-10554.
@article{8b5269d527d343e6b975096373421619,
title = "A formal synthesis of aplysiatoxin: enantioselective synthesis of kishi's aldehyde",
abstract = "This paper describes the enantioselective synthesis of key fragments (12, 18, 24, and 35) for the synthesis of aplysiatoxin (1a), a potent cancer promoter, and their convergent assembly to Kishi's aldehyde (2). Since 2 has already been transformed into 1a in a short step, its synthesis constitutes a formal total synthesis of 1a. Synthesis of fragments of aplysiatoxin (1a) and their convergent assembly to the key intermediate, Kishi's aldehyde (2), for the synthesis of 1a are described.",
author = "Hiroaki Okamura and Satoru Kuroda and Satoru Ikegami and Kenji Tomita and Sugimoto, {Yu ichi} and Sakaguchi, {Shin ichi} and Yoshio Ito and Tsutomu Katsuki and Masaru Yamaguchi",
year = "1993",
doi = "10.1016/S0040-4020(01)81547-7",
language = "English",
volume = "49",
pages = "10531--10554",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "46",

}

TY - JOUR

T1 - A formal synthesis of aplysiatoxin

T2 - enantioselective synthesis of kishi's aldehyde

AU - Okamura, Hiroaki

AU - Kuroda, Satoru

AU - Ikegami, Satoru

AU - Tomita, Kenji

AU - Sugimoto, Yu ichi

AU - Sakaguchi, Shin ichi

AU - Ito, Yoshio

AU - Katsuki, Tsutomu

AU - Yamaguchi, Masaru

PY - 1993

Y1 - 1993

N2 - This paper describes the enantioselective synthesis of key fragments (12, 18, 24, and 35) for the synthesis of aplysiatoxin (1a), a potent cancer promoter, and their convergent assembly to Kishi's aldehyde (2). Since 2 has already been transformed into 1a in a short step, its synthesis constitutes a formal total synthesis of 1a. Synthesis of fragments of aplysiatoxin (1a) and their convergent assembly to the key intermediate, Kishi's aldehyde (2), for the synthesis of 1a are described.

AB - This paper describes the enantioselective synthesis of key fragments (12, 18, 24, and 35) for the synthesis of aplysiatoxin (1a), a potent cancer promoter, and their convergent assembly to Kishi's aldehyde (2). Since 2 has already been transformed into 1a in a short step, its synthesis constitutes a formal total synthesis of 1a. Synthesis of fragments of aplysiatoxin (1a) and their convergent assembly to the key intermediate, Kishi's aldehyde (2), for the synthesis of 1a are described.

UR - http://www.scopus.com/inward/record.url?scp=0027437390&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0027437390&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(01)81547-7

DO - 10.1016/S0040-4020(01)81547-7

M3 - Article

AN - SCOPUS:0027437390

VL - 49

SP - 10531

EP - 10554

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 46

ER -