Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system

K. C. Nicolaou, J. J. Liu, Z. Yang, H. Ueno, E. J. Sorensen, C. F. Claiborne, R. K. Guy, C. K. Hwang, Masahisa Nakada, P. G. Nantermet

Research output: Contribution to journalArticle

212 Citations (Scopus)

Abstract

A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

Original languageEnglish
Pages (from-to)634-644
Number of pages11
JournalJournal of the American Chemical Society
Volume117
Issue number2
DOIs
Publication statusPublished - 1995 Jan 18
Externally publishedYes

Fingerprint

Paclitaxel
cephalomannine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Nicolaou, K. C., Liu, J. J., Yang, Z., Ueno, H., Sorensen, E. J., Claiborne, C. F., ... Nantermet, P. G. (1995). Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system. Journal of the American Chemical Society, 117(2), 634-644. https://doi.org/10.1021/ja00107a007

Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system. / Nicolaou, K. C.; Liu, J. J.; Yang, Z.; Ueno, H.; Sorensen, E. J.; Claiborne, C. F.; Guy, R. K.; Hwang, C. K.; Nakada, Masahisa; Nantermet, P. G.

In: Journal of the American Chemical Society, Vol. 117, No. 2, 18.01.1995, p. 634-644.

Research output: Contribution to journalArticle

Nicolaou, KC, Liu, JJ, Yang, Z, Ueno, H, Sorensen, EJ, Claiborne, CF, Guy, RK, Hwang, CK, Nakada, M & Nantermet, PG 1995, 'Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system', Journal of the American Chemical Society, vol. 117, no. 2, pp. 634-644. https://doi.org/10.1021/ja00107a007
Nicolaou, K. C. ; Liu, J. J. ; Yang, Z. ; Ueno, H. ; Sorensen, E. J. ; Claiborne, C. F. ; Guy, R. K. ; Hwang, C. K. ; Nakada, Masahisa ; Nantermet, P. G. / Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system. In: Journal of the American Chemical Society. 1995 ; Vol. 117, No. 2. pp. 634-644.
@article{49c3cc4db5044f2cb29d21d7c0ae0e44,
title = "Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system",
abstract = "A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.",
author = "Nicolaou, {K. C.} and Liu, {J. J.} and Z. Yang and H. Ueno and Sorensen, {E. J.} and Claiborne, {C. F.} and Guy, {R. K.} and Hwang, {C. K.} and Masahisa Nakada and Nantermet, {P. G.}",
year = "1995",
month = "1",
day = "18",
doi = "10.1021/ja00107a007",
language = "English",
volume = "117",
pages = "634--644",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system

AU - Nicolaou, K. C.

AU - Liu, J. J.

AU - Yang, Z.

AU - Ueno, H.

AU - Sorensen, E. J.

AU - Claiborne, C. F.

AU - Guy, R. K.

AU - Hwang, C. K.

AU - Nakada, Masahisa

AU - Nantermet, P. G.

PY - 1995/1/18

Y1 - 1995/1/18

N2 - A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

AB - A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

UR - http://www.scopus.com/inward/record.url?scp=0028792481&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028792481&partnerID=8YFLogxK

U2 - 10.1021/ja00107a007

DO - 10.1021/ja00107a007

M3 - Article

VL - 117

SP - 634

EP - 644

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 2

ER -