135191-48-9Relevant academic research and scientific papers
Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers
Cohen, Theodore,Tong, Shaojing
, p. 9487 - 9496 (2007/10/03)
The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2- (phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)- 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20).
Cyclopentane construction with control of side chain configuration synthesis of (+)-brefeldin A
Taber, Douglas F.,Silferberg, Lee J.,Robinson, Edward D.
, p. 6639 - 6645 (2007/10/02)
Intramolecular opening of an enantiomerically pure epoxide by an amide enolate (1 → 2) is shown to be an effective method for cyclopentane construction with control of both ring and side chain absolute configuration. This opening serves as the key step in a synthesis of the Golgi apparatus-blocking macrolide (+)-brefeldin A (3). Other features of the synthesis include improved procedures for the enantioselective hydrogenation of a β-keto ester to the corresponding β-hydroxy ester, and for the Julia-Lythgoe reduction of a β-acetoxy sulfone to the trans alkene.
