221313-83-3

Basic information

• Product Name: (1'R,2'R,3'R,6'S,7'S)-3'-Benzyloxy-4',4'-dimethylspiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-ene)
• Synonyms: (1'R,2'R,3'R,6'S,7'S)-3'-Benzyloxy-4',4'-dimethylspiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-ene)
• CAS NO: 221313-83-3
• Molecular Weight: 326.436
• Mol File: 221313-83-3.mol

Chemical Properties

• CAS DataBase Reference: (1'R,2'R,3'R,6'S,7'S)-3'-Benzyloxy-4',4'-dimethylspiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-ene)(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,2'R,3'R,6'S,7'S)-3'-Benzyloxy-4',4'-dimethylspiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-ene)(221313-83-3)
• EPA Substance Registry System: (1'R,2'R,3'R,6'S,7'S)-3'-Benzyloxy-4',4'-dimethylspiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-ene)(221313-83-3)

Safety Data

• Hazardous Substances Data: 221313-83-3(Hazardous Substances Data)

Upstream product

• 221313-79-7 (1'R,2'R,3'R,6'S,7'S)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-yl acetate 
• 221296-48-6 C₁₂H₁₆O₃ 
• 221313-82-2 C₁₄H₁₈O₃ 
• 221313-80-0 (1'R,2'R,6'S,7'S)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-en)-3'-one 
• 62928-76-1 (1'R,2'R,3'R,6'S,7'S)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-ol 
• 62928-79-4 (1'R,2'R,6'S,7'S)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-one 
• 100-39-0 benzyl bromide 
• 221313-84-4 (1'R,2'R,3'R,6'S,7'S)-4',4'-Dimethylspiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]dec-8'-en)-3'-ol 

Relevant articles and documents

Enzymatic resolution of dioxygenated dicyelopentadienes: Enantiopure hydrindanes, hydroisoquinolones, diquinanes and application to a synthesis of (+)-coronafacic acid

A 5,10-dioxygenated-tricyclo[5.2.1.02,6]decane derivative 6 has yielded to efficient enzymatic resolution to provide a range of chiral building blocks, whose absolute configuration has been determined through a total synthesis of naturally occuring (+)-coronafacic acid.

A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)-coronafacic acid and a formal synthesis of (+)-coriolin

A ready access to enantiopure 3,10-dioxygenated tricyclo[5.2.1.02,6]decane derivatives is reported. An efficient enzymatic kinetic resolution is employed through transesterification in the presence of lipase PS immobilized on Celite. Absolute configuration of the tricyclo[5.2.1.02,6]decan-10-one derivatives has been secured through correlation with (1R,2S)-1-aminoindan-2-ol. The promising utility of these enantiopure tricyclo[5.2.1.02,6]decane derivatives in synthesis has been demonstrated through the preparation of several optically pure cis-hydrindanes 15-18, employing the Haller-Bauer reaction as the key step for unbridging the trinorbornyl system. The cis-hydrindane (-)-16 has been further elaborated to the natural product (+)-coronafacic acid (+)-24. In an interesting sequence, cis-hydrindanone (+)-18 has been transformed into cis-hydroisoquinolones (+)-30 and (+)-33 via photorearrangement of the derived oxaziridines 29 and 32, respectively. The hydroisoquinolones (+)-30 and (+)-33 can serve as useful enantiopure building blocks for the synthesis of complex indole alkaloids. Oxidative cleavage of the trinorbornene double bond in the tricyclo[5.2.1.02,6]decan-10-one derivative (-)-37 and functional-group adjustments leads to the optically pure diquinane (+)-38, an advanced intermediate in the total synthesis of (+)-coriolin (+)-34.