Stereoselective synthesis of the ABCD ring framework of azaspiracids

Tetrahedron Letters

Volumn 48, Issue 30, 2007, Pages 5335-5340

  Yadav, J S ^a   Joyasawal, Sipak ^a   Dutta, S K ^a   Kunwar, A C ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

7 Membered acetonide; Acetylenic alcohol; Radical cyclization; Substituted tetrahydrofuran ring

Indexed keywords

AZASPIRACID; AZASPIRACID 1; AZASPIRACID 3; UNCLASSIFIED DRUG;

ARTICLE; ETHERIFICATION; HYDROXYLATION; REACTION ANALYSIS; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34250873297     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.021     Document Type: Article

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68. C-11H(pro-R)-C-12H(pro-R) ∼ 0 Hz and strong NOE's, C-12H(pro-S)/C-14Me, C-12H(pro-S)/C-14H, C-11H(pro-S)/C-9H(pro-S) are consistent with a twisted geometry for the five membered ring (B) with C-11 being endo to the C ring oxygen. In the six-membered ring A, C-6H shows a strong NOE correlation with the C-14 Me in the C-ring, confirming a twisted conformation such that the dihedral angles O-C6-C7-C8 has a negative magnitude whereas C7-C8-C9-C10 has a positive value. The NOE correlations and geometries of the A-D rings in the energy minimized structure of 3 are shown in Figures 2 and 3, respectively.