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Most Requested Journal Articles 2Q04-Chemistry and Related

Following is one of the journal articles most requested by researchers using CAS online services.

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CAS indexed 125 chemical substances from this document. CAS subject entries for this document include: Resolution (separation); Asymmetric synthesis and induction; Horner Emmons reaction; and 3 additional concepts.

CAPLUS COPYRIGHT 2004 ACS on STN

TITLE:	Enantioselective Total Synthesis of the Antitumor Macrolide Rhizoxin D
AUTHOR(S):	Lafontaine, Jennifer A.; Provencal, David P.; Gardelli, Cristina; Leahy, James W.
CORPORATE SOURCE:	Department of Chemistry, University of California, Berkeley, CA, 94720-1460, USA
SOURCE:	Journal of Organic Chemistry (2003), 68(11), 4215-4234 CODEN: JOCEAH; ISSN: 0022-3263
PUBLISHER:	American Chemical Society
LANGUAGE:	English

ABSTRACT:
The convergent, highly enantioselective synthesis of rhizoxin D, a natural product possessing potent antitumor and antifungal bioactivity, is described. The C(1)-C(9) fragment of the mol. was synthesized utilizing a threefold pseudosym. intermediate ultimately derived from .gamma.-butyrolactone. The central core of rhizoxin D was prepd. via a chiral resoln./asym. aldol protocol. Several methods for the generation of the polyene fragment were explored, and the side-chain was ultimately prepd. from serine in six steps. The unification of the left and right wings of the mol. was achieved using a one-step olefination protocol, and the macrocyclization was carried out using a Horner-Emmons olefination at the C(2)-C(3) olefin.

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