130877-15-5

Basic information

• Product Name: (1R,8aR)-1-Furan-3-yl-8a-methyl-5-methylene-6-((1S,5R,6R)-6,9,9-trimethyl-3-oxo-2-oxa-bicyclo[3.3.1]non-7-en-6-yl)-1,5,6,7,8,8a-hexahydro-isochromen-3-one
• CAS NO: 130877-15-5
• Molecular Weight: 422.521
• Mol File: 130877-15-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,8aR)-1-Furan-3-yl-8a-methyl-5-methylene-6-((1S,5R,6R)-6,9,9-trimethyl-3-oxo-2-oxa-bicyclo[3.3.1]non-7-en-6-yl)-1,5,6,7,8,8a-hexahydro-isochromen-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,8aR)-1-Furan-3-yl-8a-methyl-5-methylene-6-((1S,5R,6R)-6,9,9-trimethyl-3-oxo-2-oxa-bicyclo[3.3.1]non-7-en-6-yl)-1,5,6,7,8,8a-hexahydro-isochromen-3-one(130877-15-5)
• EPA Substance Registry System: (1R,8aR)-1-Furan-3-yl-8a-methyl-5-methylene-6-((1S,5R,6R)-6,9,9-trimethyl-3-oxo-2-oxa-bicyclo[3.3.1]non-7-en-6-yl)-1,5,6,7,8,8a-hexahydro-isochromen-3-one(130877-15-5)

Safety Data

• Hazardous Substances Data: 130877-15-5(Hazardous Substances Data)

Upstream product

• 6488-67-1 deoxyandirobin 
• 67-63-0 isopropyl alcohol 

Relevant articles and documents

A Synthesis of Methyl 2α-Acetoxy-3-deoxo-3α-hydroxyangolensate

The title compound (1a) has been partially synthesised from gedunin.It is the first natural 1α,2α,3α-trihydroxy terpene molecule to have been synthesised.Attempts to introduce a 2α-hydroxy group into a preformed methyl angolensate derivative failed, and the synthesis was achieved by the prior preparation of 2α-acetoxy-7-deacetoxy-7-oxokhivorin (2a), which was converted into the title compound.The key stage in the conversion is the Baeyer-Villiger oxidation of the 7-oxo group to a lactone, which was studied in some detail.The use of buffered peracetic acid effects the required oxidation in good yield without oxidising the furan ring; the use of pertrifluoroacetic acid oxidises the furan ring to an unsaturated lactone without attacking the carbonyl group.The implications of this are considered in an Appendix.