1.
Org Lett
; 15(8): 2046-9, 2013 Apr 19.
Article
in English
| MEDLINE
| ID: mdl-23560679
ABSTRACT
An efficient strategy for the total synthesis of (-)-blepharocalyxin D and an analogue is described. The key step involves an acid-mediated cascade process in which reaction of methyl 3,3-dimethoxypropanoate with γ,δ-unsaturated alcohols possessing diastereotopic styrenyl groups gives trans-fused bicyclic lactones with the creation of two rings and four stereocenters in one pot.
Subject(s)
Alcohols/chemistry , Lactones/chemical synthesis , Pyrans/chemical synthesis , Alpinia/chemistry , Lactones/chemistry , Molecular Structure , Pyrans/chemistry , Stereoisomerism
2.
Angew Chem Int Ed Engl
; 51(16): 3901-4, 2012 Apr 16.
Article
in English
| MEDLINE
| ID: mdl-22392806
ABSTRACT
trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework.