Total synthesis of (-)-spirangien A and its methyl ester.
The first total synthesis of (-)-spirangien A, a cytotoxic and antifungal polyketide of myxobacterial origin, is reported; this exploits a Stork-Wittig olefination and double Stille cross-coupling sequence to install the sensitive pentaene side chain onto a fully elaborated spiroacetal core, leading initially to the methyl ester of spirangien A.
Paterson
Ian
I
University Chemical Laboratory, Lensfield Road, Cambridge, UK. ip100@cam.ac.uk
Findlay
Alison D
AD
Noti
Christian
C
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure
D000080:Acetals; D004952:Esters; D005231:Fatty Acids, Unsaturated; C523683:spirangien A