The synthesis of (-)-sirenin. sperm attractant of the water mold allomyces macrogynus

✍ Scribed by Takeshi Kitahara; Akira Horiguchi; Kenji Mori

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 724 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86174-3

✦ Synopsis

MNtzact --SyntheslS of (-)-slnmln La, sperm attracting hotmcmc of AllcmYcea mbrro_ m was achwved thmqh 10 steps frm I-I-per~llaldehyde 3. Fornatxm of CyCb ~~qxme rlnq was executed dlastereorlecuvely by the ~yrlm.aLm !JL_+ mt.ramolesxlar epou& opml*g rrnder Carefully antrolled and1t1a Sirenin la is a powerful sperm attractant produced by the female qamates of the water mold Allomyces macrogynus and active at concentration of 10-l" M.') Machlls, Rapoport and co-workers described the isolation and characterization of sirenin la and its 4-(knitro-DhenylazoEmnzoate (NABS)*) and then the structural elucidation. )l The absolute confiquration was rigorously assigned by the synthesis of both the enantiomers of la via optical resolution and CD spectral studies of the intermediate.3c1 As la has extremely interesting biological activity, many efforts have been devoted to its synthesis.3c~41 nost of them, however, were the synthesis of (:)-la except for one by Rapoport et a1.3c1 --1.44 (2H, rn), 1.46 (2H. br.s), 1.67 (3H. s), 1.69-1.92 (2H. m), 2.00-2.07 IlH, ml, 2.12 (2t1, df,