The synthesis of (−)- cis- and (−)- trans-crobarbatic acid

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The synthesis of (−)- cis- and (−)- trans-crobarbatic acid

Donohoe, Timothy J; Stevenson, Clare A; Helliwell, Madeleine; Irshad †, Ranah; Ladduwahetty, Tamara

Tetrahedron: asymmetry, 04/1999, Volume: 10, Issue: 7

Journal Article

The synthesis of both cis- and trans-crobarbatic acid is reported. The five-step sequence proceeds in high yield and with control of both relative and absolute stereochemistry. The key step in the synthesis is the Birch reductive alkylation of a chiral furoic acid which sets the absolute stereochemistry of the products. The stereochemistry of the compounds described was proven unambiguously by X-ray crystallography on one synthetic intermediate and on trans-crobarbatic acid.

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Donohoe, Timothy J | Stevenson, Clare A | Helliwell, Madeleine | Irshad †, Ranah | Ladduwahetty, Tamara

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