An approach to the synthesis of the hexahydronaphthalene unit of pravastatin

DOI: 10.1016/0040-4039(90)80194-Q

Source and publish data:

Tetrahedron Letters p. 2235 - 2238 (1990)

Update date:2022-08-05

Topics: Hydrogenation Stereochemistry Control Ring Formation Functional Group Transformations Protecting group strategy Final Adjustments

Authors:

Barrish, Joel C.

Wovkulich, Peter M.

Tang, Peng Cho

Batcho, Andrew D.

Uskokovic, Milan R.

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Article abstract of DOI:10.1016/0040-4039(90)80194-Q

The aldehyde 3b is prepared from (S)-pulegone (5) by a series of highly effective transformations, including a stereospecific [2,3]-Wittig rearrangement of the allyl ether of 6, stereoselective selenolactonization of 8c, SN2′ addition to 10 and a stereospecific intramolecular ene reaction of 11b.

Full text of DOI:10.1016/0040-4039(90)80194-Q

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