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Titolo:
Asymmetric total synthesis of halicholactone
Autore:
Baba, Y; Saha, G; Nakao, S; Iwata, C; Tanaka, T; Ibuka, T; Ohishi, H; Takemoto, Y;
Indirizzi:
Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan Osaka Univ Suita Osaka Japan 5650871 eut Sci, Suita, Osaka 5650871, Japan Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan Kyoto Univ Kyoto Japan 6068501 aceut Sci, Sakyo Ku, Kyoto 6068501, Japan Osaka Univ Pharmaceut Sci, Takatsuki, Osaka 5691094, Japan Osaka Univ Pharmaceut Sci Takatsuki Osaka Japan 5691094 ka 5691094, Japan
Titolo Testata:
JOURNAL OF ORGANIC CHEMISTRY
fascicolo: 1, volume: 66, anno: 2001,
pagine: 81 - 88
SICI:
0022-3263(20010112)66:1<81:ATSOH>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
ORGANIC-SYNTHESIS; NATURAL-PRODUCTS; COMPLEXES; NEOHALICHOLACTONE; ACID; STEREOCONTROL; METATHESIS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
38
Recensione:
Indirizzi per estratti:
Indirizzo: Tanaka, T Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamada Oka, Suita, Osaka 5650871,Japan Osaka Univ 1-6 Yamada Oka Suita Osaka Japan 5650871 650871,Japan
Citazione:
Y. Baba et al., "Asymmetric total synthesis of halicholactone", J ORG CHEM, 66(1), 2001, pp. 81-88

Abstract

The asymmetric total synthesis of the marine metabolite, halicholactone 1,is described. The bisallylic triol 6 with three chiral centers at C8, C12,and C15 was constructed by [2,3]-sigmatropic rearrangement of the sulfoxide 18, which was prepared stereoselectively using the chirality of (diene)Fe(CO)(3) complexes. Introduction of the trans-substituted cyclopropane subunit into 21 was successfully achieved using the modified regio- and stereoselective Simmons-Smith reaction. The use of RCM (ring-closing metathesis) methodology (4 --> 35) was pivotal for the formation of a nine-membered unsaturated lactone fragment of halicholactone 1. As this approach is flexible and stereoselective, other oxylipins could be synthesized by the protocol described herein.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/09/20 alle ore 08:17:00