A CONCISE TOTAL SYNTHESIS OF (-)-CIS-CLAVICIPITIC AND (+-)-TRANS-CLAVICIPITIC ACIDS BY COMBINATIONAL USE OF DIRECTED LITHIATION AND FLUORIDE ION-INDUCED ELIMINATION-ADDITION REACTION OF 1-(TRIISOPROPYLSILYL)GRAMINE DERIVATIVES()

Authors
IWAO M ISHIBASHI F
Citation
M. Iwao et F. Ishibashi, A CONCISE TOTAL SYNTHESIS OF (-)-CIS-CLAVICIPITIC AND (+-)-TRANS-CLAVICIPITIC ACIDS BY COMBINATIONAL USE OF DIRECTED LITHIATION AND FLUORIDE ION-INDUCED ELIMINATION-ADDITION REACTION OF 1-(TRIISOPROPYLSILYL)GRAMINE DERIVATIVES(), Tetrahedron, 53(1), 1997, pp. 51-58
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
1
Year of publication
1997
Pages
51 - 58
Database
ISI
SICI code
0040-4020(1997)53:1<51:ACTSO(>2.0.ZU;2-8
Abstract
A six-step total synthesis of (+/-)-clavicipitic acid (1) from 1-(trii sopropylsilyl)gramine (2) was achieved by combinational use of 4-selec tive lithiation of 2 and fluoride ion-induced elimination-addition rea ction of -hydroxy-3-methyl-1-butenyl]-1-(triisopropylsilyl) (7) as key reactions. Separation of cis- and trans-diastereomers (1a and 1b) wer e easily accomplished by simple fractional crystallization and column chromatography. The overall yields of 1a and 1b from 2 were 21% and 17 %, respectively. Copyright (C) 1996 Elsevier Science Ltd