Addition of Chiral Allyltrichlorostannanes to Chiral Aldehydes : total syntheseis of (+)-Prelactone B / Adição de aliltriclorestanana quirais a aldeidos quirais : sintese total da (+)-prelactona B

AUTOR(ES)
DATA DE PUBLICAÇÃO

2006

RESUMO

The Lewis-acid mediated reaction of allylsilanes and allylstannanes with aldehydes is a well-known procedure for the preparation of homoallylic alcohols. Chiral allyltrichlorostannanes react with chiral a-methyl, b-alkoxy and syn and anti a-methyl-b-alkoxy aldehydes to give the corresponding homoallylic alcohols with moderate to high 1,4-syn-diastereoselectivities. The asymmetric total synthesis of (+)-prelactona B, a biologically important natural b-hydroxy-d-lactone derivative that contains a 2,3-trans-dialkylpyran ring system, has been achieved in seven steps and 33% overall yield. This approach involves the use of a very efficient oxazolidinone-mediated anti-aldol reaction, and a diastereoselective coupling between a ketene silyl acetal with the aldehyde (-)-79 followed by lactonization.

ASSUNTO(S)

diastereoselectivity allytrichloroetannanes diastereosseletividade prelactone b alitricloroetananas prelactona b

ACESSO AO ARTIGO

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