First asymmetric total synthesis of aspergillide D.
The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from d-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. mohapatra@iict.res.in.
Bighnanshu K
BK
Jena
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. mohapatra@iict.res.in.
G Sudhakar
GS
Reddy
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. mohapatra@iict.res.in.
Debendra K
http://orcid.org/0000-0002-9515-826X
DK
Mohapatra
D007700:Kinetics; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012266:Ribose / Q000737:chemistry
D018942:Macrolides; C584639:aspergillide D; D012266:Ribose