Intermediates and improved processes for the preparation of...

Details Intermediates and improved processes for the preparation of... Intermediates and improved processes for the preparation of...

Filed on

2006-05-30

Date issued

2006-05-30

Examiner

Saucier, Sandra E. (Department: 1651)

Patent Class

Organic compounds -- part of the class 532-570 series

SubClass

Organic compounds

SubSubClass

Heterocyclic carbon compounds containing a hetero ring...

Other Related Categories

C549S214000, C435S280000

Type

Reexamination Certificate

Status

active

Patent number

07053224

Description

ABSTRACT:
Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-[(dimethylmethylene)dioxy]-5-hydroxy-tricyclo[5.2.1.02,6dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo[5.2.1.02,6]deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.

REFERENCES:
patent: 5300664 (1994-04-01), Takano et al.
“Lipase-Mediated Kinetic Resolution of a Synthetic Equivalent of 2-Hydroxymethylcyclopentadien-5-ol”, by Yoshida et al., Tetrahedron: Asymmetry 9 (1998), pp. 3325-3329.
“A Concise Synthesis of (-)-Neplanocin A”, by Yoshida et al., Tetrahedron Letters 39 (1998), pp. 4677-4678.
“Total Synthesis of (-)-Neplanocin A from L-Ribulose”, by Vandewalle et al., Synlett (Dec. 1991), pp. 921-922.
“Synthesis of (-)-Neplanocin A via C-H Insertion of Alkylidenecarbene”, by Ohira et al., Tetrahedron Letters, vol. 36, No. 9 (1995), pp. 1537-1538.
“An Enantio- and Diastereo-Controlled Synthesis of (-) Neplanocin A and its 2,3-Di-Epi-Isomer”, by Trost et al., Tetrahedron Letters, vol. 38, No. 10 (1997), pp. 1707-1710.
“Nucleophilic Eliminative Ring Fission of Bridgehead Substituted 1,3-Bishomocubyl Acetates”, by Klunder et al., Tetrahedron, vol. 41, No. 5 (1985), pp. 963-973.

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