Synthesis of (+/-)-africanol

Two diastereomers of africanol, compounds 1a and 1b, were obtained exclusively through a methodology which employed, as the key step, the (BuLi)-Bu-n mediated intramolecular cyclization of the vinyl iodide 5. A similar cyclization of 19 provided exclusively the tertiary allylic alcohol 20. Africanol...

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Bibliographic Details
Published inJournal of the Brazilian Chemical Society Vol. 11; no. 5; pp. 502 - 511
Main Authors Marques, FD, Ferreira, JTB, Piers, E
Format Journal Article
LanguageEnglish
Published SAO PAULO Soc Brasileira Quimica 01.01.2000
Sociedade Brasileira de Química
Subjects
africanol
Chemistry
CHEMISTRY, MULTIDISCIPLINARY
cyclization
Physical Sciences
samarium iodide
Science & Technology
synthesis
synthesis
KETONES
CARBONYL-COMPOUNDS
samarium iodide
africanol
cyclization
CONJUGATE ADDITION
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Summary:Two diastereomers of africanol, compounds 1a and 1b, were obtained exclusively through a methodology which employed, as the key step, the (BuLi)-Bu-n mediated intramolecular cyclization of the vinyl iodide 5. A similar cyclization of 19 provided exclusively the tertiary allylic alcohol 20. Africanol could be prepared, along with its diastereomers 1a and 1b, when ketone 21 was submitted to the cyclization reaction promoted by samarium iodide.
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50532000000500012