Asymmetric synthesis of (+)-altholactone, a styryllactone from various goniothalamus species

A consice and stereoselective route to highly functionalised a,b-unsaturated-d-lactone, (+)-altholactone (1), from the well-established 1,3-diol building block, dioxanone (2,2-dimethyl-1,3-dioxan-5-one) 4, is described. This approach is based on establishment of the chiral centres by applying a RAMP-directed alkylation (ee > 98 %), an asymmetric aldol reaction (ee, de > 98 %) and a selective reduction (de > 96 %). The d-lactone, which is the main motif of the styryllactone family, results from an oxidation/in situ cyclisation sequence and the furanic cycle from an SN2 ring-closure.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2006

Author dc:creator

• Barbion, Julien

Contributors dc:contributor

• Enders, Dieter

• info:eu-repo/classification/ddc/540
• Chemie
• asymmetric synthesis
• Styryllactone
• asymmetric alkylation
• aldol reaction

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123198%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:61543