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Hydrolysis and Rearrangement Reactions of Caryophyllene Oxide

“…The nmr data for 1-5 and 7 are consistent with those reported in the literature (1)(2)(3)(4)(5) (Scheme 1). The 13C-nmr resonances of 6, a compound that has not been reported previously, indicate that the exomethylene double-bond from caryophyllene oxide remained unchanged.…”

“…Compounds 6 and 7 were the major products in the hydrolysis of caryophyllene oxide, and constituted 42% of the total gc peak area and 73% of the isolated products by weight. Compounds 4 and 5 have previously been reported as by-products in the oxidation of caryophyllene by lead tetraacetate (1). They are apparently the elimination products of the carbocation with the charge at C-4.…”

Structures of Two Novel Sesquiterpenoids Formed by the Lead Tetraacetate Oxidation of β-Caryophyllene

“…Namely, caryophylla-8( 13)-ene-4,5-epoxide (2) was found in Zingeber zerumbet Smith,4) caryophylla-4( 12),8( 13)-dien-5a-ol (8), caryophylla-3,8( 13)-dien-5a-ol (10), and caryophylla-3,8(13)-dien-5 [3-01 (11) in china gum terpentine,5,6) and caryophylla-4,8(13)-dien-7-01 (12) in clove and hop oils. 7 ) Recently, two crystalline, minor products (14 and 15) were newly obtained by theoxidation products of [3-caryophyllene (1) with lead tetraacetate, and we report here the structures and absolute configurations of these two crystalline products.…”

Structures of two novel sesquiterpenoids formed by the lead tetraacetate oxidation of .BETA.-caryophyllene.

“…(2) was found in Zingeber zerumbet Smith,4) caryophylla-4(12),8 (1 3)-dien-5a-ol (8), caryophylla-3,8(1 3)dien-5a-ol (10), and caryophylla-3,8(13)-dien-5/?-ol (ll) in china gum terpentine, 5 6) and caryophylla-4,8(13)-dien-7-ol (12) in clove and hop oils.7)…”