A norbornyl route to cyclohexitols: Stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3509-3512

  Mehta, Goverdhan ^a   Lakshminath, Sripada ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Cyclitols; Fragmentation reactions; Hydroxylation

Indexed keywords

CONDURITOL E; GABOSINE B; INOSITOL DERIVATIVE; MK 7607; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034728955     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00409-3     Document Type: Article

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18. 7 for gabosine K: δ H (200 MHz, CD 3 OD): 2.06 (s, 9-H 3), 3.39 (m, 2H, J 8, 6.5, 3-H and 4-H), 4.04-4.18 (m, 2H, 1-H and 2-H), 4.53/4.73 (2 d, J AB 13.5, m, 7-H 2), 5.59 (m, 6-H); δ C (50.3 MHz, CD3OD): 172.5, 136.2, 128.8, 77.5, 77.1, 73.5, 73.0, 64.8, 20.8. These spectral data reveal that the two compounds though not identical, do share common structural features indicating that the natural product may have a stereoisomeric structure related to 18.