Diol formation, stereochemistry conformational effects

Tetrahydronaphthalene epoxide hydrolysis conformational effects on stereochemistry of diol formation 267... 

TETRAHYDRONAPHTHALENE EPOXIDE HYDROLYSIS CONFORMATIONAL EFFECTS ON STEREOCHEMISTRY OF DIOL FORMATION... 

The presence of acetate substituents on the side chain at C-6 is very common. Compounds (40) and (41) were isolated by Drewes et al from the bark of Cryptocarya latifolia trees in their investigations of the chemistry of plants used for magical and medicinal purposes by the Zulu people (55). The CD spectra of these two compounds show a positive Cotton effect and hence they possess the (67 )-configuration. Saponification followed by acetonide formation of (40) afforded two acetonides (42) and (43) (50). A (2 7 ,6 5)-stereochemistry followed from application of the MTPA determination rule (24) to the (/ )- and (5)-MTPA esters of these acetonides. A (4 5)-stereochemistry was assigned from the syn-diol relationship of the two acetal oxygen atoms in (42) and (43) as determined from their C NMR spectra (57). Thus the acetonide rings in both compounds possessed chair conformations with the alkyl... 

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See also in sourсe #XX -- [ , , ]

See also in sourсe #XX -- [ , , ]

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