4705-06-0Relevant articles and documents
Asymmetric total synthesis and X-ray crystal structure of the cytotoxic marine diterpene (+)-vigulariol
Becker, Jochen,Bergander, Klaus,Froehlich, Roland,Hoppe, Dieter
supporting information; experimental part, p. 1654 - 1657 (2009/02/06)
(Figure Presented) A crystal from the China sea: The asymmetric total synthesis of (+)-vigulariol (see picture: red O, blue C, white H) has been accomplished in eight linear steps starting from (R)-cryptone, which is readily available from eucalyptus oil. Key steps involve an asymmetric homoaldol reaction of chiral allyl carbamates and THF cyclocondensation. Ring-closing metathesis led to the tricyclic framework of the cladiellin diterpenes.
FLUOROSULFONIC ACID INDUCED RING OPENING OF PINANONES: PINANE CHIRALITY IN SYNTHESIS
Coxon, James M.,Hydes, Graeme J.,Steel, Peter J.
, p. 5213 - 5218 (2007/10/02)
The acid-catalysed ring opening of a number of substituted nopinones to give 4-(2-propyl)cyclohex-2-enones is described.In an application of this reaction use has been made of pinane chirality in the synthesis of R-o-mentha-2,4-diene (13) by fluorosulfonic acid-catalysed rupture of cis-verbanone (8) to (4S,5R)- and (4R,5R)-5-methyl-4(2-propyl)cyclohex-2-enone (9 and 10) followed by reduction-elimination.