What is the absolute configuration of (+)-crispatanolide isolated from Makinoa crispata (liverwort)?

Authors :: Nakashima, Katsuyuki
Kawano, Hiroyuki
Kumano, Minako
Kodama, Hikari
Kameoka, Masayo
Yamamoto, Akiyo
Mizutani, Reiko
Sono, Masakazu
Tori, Motoo
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Aug2015, Vol. 56 Issue 34, p4912-4915. 4p.
Publication Year :: 2015
Abstract: Crispatanolide, which was isolated from Makinoa crispata (liverwort) in 1980, was synthesized in its chiral form starting from 3-substituted-2-bromocyclohex-2-en-1-one using CBS reduction. The absolute configuration was established using the modified Mosher method on the CBS reduction product. This synthesis established the absolute configuration of the natural product, which is presumably derived from a 10β-methyl-7-βH-eudesmane type precursor. [ABSTRACT FROM AUTHOR]

Subjects :: *CHIRALITY
*SUBSTITUTION reactions
*CYCLOHEXENONES
*CHEMICAL reduction
*EUDESMANES

Language :: English
ISSN :: 00404039
Volume :: 56
Issue :: 34
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 108432231
Full Text :: https://doi.org/10.1016/j.tetlet.2015.06.083

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