STUDIES ON THE TERPENOIDS AND RELATED ALICYCLIC COMPOUNDS .44. TOTAL SYNTHESIS OF (+ -)-CEMBRANOLIDE VIA CR(II) MEDIATED INTRAMOLECULAR MACROCYCLIZATION OF BETA-ALKOXYCARBONYLALLYL HALIDE/

Authors
NISHITANI K KONOMI T MIMAKI Y TSUNODA T YAMAKAWA K
Citation
K. Nishitani et al., STUDIES ON THE TERPENOIDS AND RELATED ALICYCLIC COMPOUNDS .44. TOTAL SYNTHESIS OF (+ -)-CEMBRANOLIDE VIA CR(II) MEDIATED INTRAMOLECULAR MACROCYCLIZATION OF BETA-ALKOXYCARBONYLALLYL HALIDE/, Heterocycles, 36(9), 1993, pp. 1957-1960
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
36
Issue
9
Year of publication
1993
Pages
1957 - 1960
Database
ISI
SICI code
0385-5414(1993)36:9<1957:SOTTAR>2.0.ZU;2-E
Abstract
The omega-formyl-beta-methoxycarbonylallyl halide (20), prepared from geraniol and methyl beta-hydroxypropionate, was cyclized efficiently a nd with high stereoselectivity to 14-membered cis-cycloalkenol (21) by CrCl2 in DMF. The cycloalkenol was treated with p-TsOH to give an exc ellent yield of (+/-)-cis-cembranolide (VI).