First enantioselective total synthesis of both (+)- and (-)-metachromin A

Article abstract of DOI:10.1002/1099-0690(200102)2001:4<647::AID-EJOC647>3.0.CO;2-6

The antineoplastic agent (-)-metachromin A (1) from Hippospongia metachromia has been synthesized in enantiomerically pure form in 13% overall yield. A general convergent synthetic strategy for different metachromins using a 2-alkyloxy-3-sulfonyl-l,3-oxazolidine as a chiral dithienium equivalent is presented.