Simple total synthesis of the pentacyclic C(s)-symmetric structure attributed to the squalenoid glabrescol and three C(s)-symmetric diastereomers compel structural revision

Journal of the American Chemical Society

Volumn 122, Issue 19, 2000, Pages 4831-4832

  Xiong, Zhaoming ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMOBENZOIC ACID DERIVATIVE; EPOXIDE; ISOPRENOID; SQUALENE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034678998     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000842y     Document Type: Article

References (14)

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3. Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
4. The enantioselectivity of the epoxidation of each double bond in the conversion of 2 to 4 can be estimated as > 20:1.
5. Generously provided by Dr. Helen Jacobs, University of the West Indies.
6. Detailed X-ray crystallographic data are available from the Cambridge Cristallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ, U.K.
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9. Alternatively, the (S,S)-diepoxide 8 can be obtained from a mixture of isomeric epoxides by preparative HPLC separation on a Chiral Technologies Chiralpak AS column.
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11. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
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13. (b) Pasto, D. J.; Taylor, R. T. Org. Reactions 1991, 40, 91.
14. Koert, U. Synthesis 1995, 115.