89656-03-1Relevant articles and documents
THE TOTAL SYNTHESIS OF (+/-)-COLORATA-4(13),8-DIENOLIDE
Groot, Ae. de,Broekhuysen, M. P.,Doddema, L. L.,Vollering, M. C.,Westerbeek, J. M. M.
, p. 4831 - 4834 (1982)
The total synthesis of (+/-)-colorata-4(13),8-dienolide (1), a sesquiterpene with a rearranged drimane skeleton, is described using 6β, 8aβ-dimethyl-5-methylene-3,4,4aα,5,6,7,8,8a-octahydro-1(2H)-naphtalenone (10) as a key intermediate.A new annelation me
A Stereoselective Total Synthesis of (+/-)-Muzigadial
Bosch, M. Pilar,Camps, Francisco,Coll, Jose,Guerrero, Angel,Tatsuoka, Toshio,Meinwald, Jerrold
, p. 773 - 784 (2007/10/02)
A stereoselective 14-step, total synthesis of (+/-)-muzigadial (1a, 11percent overall yield), starting from the commercially available Wieland-Miescher ketone (5), via intermediate ketone 13, is described.The two additional chiral centers in 13 were incorporated by equilibrium of the mixture of stereoisomeric ketones 10 to the most favorable isomer, 10a.The key step for introducing the necessary functionality at C-1 involved the regio- and stereoselective cis hydroxylation of enol ether 37b with osmium tetraoxide in the presence of tert-butyl hydroperoxide.