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Titolo:
Chemoenzymatic synthesis of (+)-docosa-4,15-dien-1-yn-3-ol, a component ofthe marine sponge Cribrochalina vasculum, and confirmation of the structure and absolute configuration of the acetylenic alcohol, by lipase-catalysedbiotransformations
Autore:
Morishita, K; Kamezawa, M; Ohtani, T; Tachibana, H; Kawase, M; Kishimoto, M; Naoshima, Y;
Indirizzi:
Okayama Univ Sci, Fac Informat, Okayama 7000005, Japan Okayama Univ Sci Okayama Japan 7000005 Informat, Okayama 7000005, Japan Konan Chem Ind Co Ltd, Takatsuki, Osaka 5690066, Japan Konan Chem Ind Co Ltd Takatsuki Osaka Japan 5690066 Osaka 5690066, Japan
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 4, , anno: 1999,
pagine: 513 - 518
SICI:
0300-922X(19990221):4<513:CSO(AC>2.0.ZU;2-V
Fonte:
ISI
Lingua:
ENG
Soggetto:
PSEUDOMONAS-CEPACIA LIPASE; ENANTIOMERS; STEREOCHEMISTRY; HYDROLYSIS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
16
Recensione:
Indirizzi per estratti:
Indirizzo: Naoshima, Y Okayama Univ Sci, Fac Informat, 1-1 Ridai Cho, Okayama 7000005, Japan Okayama Univ Sci 1-1 Ridai Cho Okayama Japan 7000005 5, Japan
Citazione:
K. Morishita et al., "Chemoenzymatic synthesis of (+)-docosa-4,15-dien-1-yn-3-ol, a component ofthe marine sponge Cribrochalina vasculum, and confirmation of the structure and absolute configuration of the acetylenic alcohol, by lipase-catalysedbiotransformations", J CHEM S P1, (4), 1999, pp. 513-518

Abstract

The (4E,15Z)- and (4E,15E)-isomers of (+)-docosa-4,15-dien-1-yn-3-ol 1, isolated from the marine sponge Cribrochalina vasculum, were synthesized in highly enantiomerically pure form by lipase-mediated biotransformation with Novozym 435, and the structure of 1 from the natural product was proved to be (4E,15Z)-docosa-4,15-dien-1-yn-3-ol 1Z. The absolute configuration of C-3 in compound (+)-1Z was assigned as S on the basis of the conversion of (+)-1Z into (R)-(-)-docosan-3-ol 17, which was also prepared from oct-7-en-3-ol 12 via biotransformation with lipase Novozym.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 28/11/20 alle ore 00:51:44