Total synthesis of (R,R)-crinan via regiospecific and stereoselective palladium catalysed cyclisation

DOI: 10.1016/S0040-4020(01)81882-2

Source and publish data:

Tetrahedron p. 5177 - 5188 (1993)

Update date:2022-09-26

Topics:

Authors:

Grigg Grigg

Santhakumar

Sridharan

Thornton-Pett

Bridge Bridge

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Article abstract of DOI:10.1016/S0040-4020(01)81882-2

The synthesis of (R,R)-crinan from (S)-1-cyclohexenylethan-1-ol is described. The key palladium catalysed step involves a regiospecific 6-exo trig cyclisation which proceeds with 20:1 stereoselectivity for the trans-ring junction over the cis-ring fusion. The ring junction stereochemistry is sensitive to solvent, phosphine and small amounts of water.

Full text of DOI:10.1016/S0040-4020(01)81882-2

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