221297-63-8

Upstream product

• 100-46-9 benzylamine 
• 221297-02-5 Methyl (1S,6S)-7-oxobicyclo[4.3.0]non-2-ene-2-carboxylate 
• 221296-78-2 (1R,2R,6R,7S)-Tricyclo[5.2.1.0^2,6]dec-8-en-3,10-dione 
• 221296-71-5 (1R,2R,3R,6S,7S)-3-Hydroxytricyclo[5.2.1.0^2,6]dec-8-en-10-one 
• 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 
• 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 
• 221313-80-0 (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 
• 221296-98-6 Methyl (1S,6S,7R)-7-hydroxybicyclo[4.3.0]non-2-ene-2-carboxylate 
• 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 

Downstream Products

• 221297-66-1 Methyl (4aS,8aS)-2-benzyl-1-oxo-1,2,3,4,4a,7,8,8a-octahydroisoquinoline-5-carboxylate 

Relevant academic research and scientific papers

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.

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.