Practical enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis- 4,5-diamino-2-cyclopenten-1-ol derivative.
An enantiospecific synthesis of an orthogonally protected 1,4-trans-1,5-cis-4,5-diamino-2-cyclopenten-1-ol derivative 16 is reported. The trans-diamine moiety was established by anti-specific vinyl addition to a novel threitol-derived tert-butanesulfinylimine 2 and Overman rearrangement. The cyclopentene skeleton was constructed via RCM reaction of a key 1,6-diene intermediate 11.
Wang
Bing
B
Shanghai Boramino Chemicals Co., Ltd., Room 202, Unit 5, Building 1, 688 Qiushi Road, Shanghai 201512, China. boramino10@yahoo.com
D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D003959:Diamines / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*
C553941:1,4-trans-1,5-cis- 4,5-diamino-2-cyclopenten-1-ol; D003517:Cyclopentanes; D003959:Diamines; D013402:Sugar Alcohols; C003460:threitol