The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the southern hemisphere EF segment.
The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 , incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.
University Chemical Laboratory, Lensfield Road, University of Cambridge, Cambridge, UKCB2 1EW. ip100@cam.ac.uk
Ian
I
Paterson
Mark J
MJ
Coster
David Y-K
DY
Chen
José L
JL
Aceña
Jordi
J
Bach
Linda E
LE
Keown
Thomas
T
Trieselmann
D000080:Acetals / Q000138:chemical synthesis; D000438:Alcohols / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001895:Boron / Q000737:chemistry; D007700:Kinetics; D018942:Macrolides / Q000138:chemical synthesis*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism; D013816:Thermodynamics; D000095702:Polyether Toxins
D000080:Acetals; D000438:Alcohols; D000970:Antineoplastic Agents; D001895:Boron; D018942:Macrolides; D011714:Pyrans; D013141:Spiro Compounds; C083856:spongistatin 1; D000095702:Polyether Toxins