TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-CIS-CEMBRANOLIDES, TRANS-CEMBRANOLIDES AND (PLUS-OR-MINUS)-SARCOPHYTONIN-B FROM GERANYLGERANIOL

Authors
NISHITANI K KONOMI T OKADA K YAMAKAWA K
Citation
K. Nishitani et al., TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-CIS-CEMBRANOLIDES, TRANS-CEMBRANOLIDES AND (PLUS-OR-MINUS)-SARCOPHYTONIN-B FROM GERANYLGERANIOL, Heterocycles, 37(2), 1994, pp. 679-681
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
37
Issue
2
Year of publication
1994
Pages
679 - 681
Database
ISI
SICI code
0385-5414(1994)37:2<679:TSO(T>2.0.ZU;2-8
Abstract
(+/-)-cis-Cembranolide (I) was synthesized via Cr(II) mediated intramo lecular macrocyclization of omega-formyl-beta-methoxycarbonylallyl hal ides (6a and b), which were prepared starting from geranylgeraniol. Th e stereoselective synthesis of (+/-)-trans-cembranolide (II) was achie ved by lactonization of 14-membered cis-intermediate (7) with inversio n of the stereochemistry at C-2. (+/-)-Sarcophytonin B (III) was also synthesized from (+/-)-cis-cembranolide (I) via isomerization of the e xo-cyclic double bond.