Über die endo-exo-Isomerie bei Verbindungen vom Camphertypus. II. Die Konfiguration des Borneols und Isoborneols.

Camphor: a chiral starting material in natural product synthesis

“…Oxidation of (-)-bornyl acetate (8 1) with CrO, and or with CrO,, HOAc, and Ac2081-86 provides a mixture of 5oxobornyl acetate (83) [24-40% yield], 6-oxobornyl acetate (84) [5-15% yield], and other minor products86 (Scheme 17). Remote oxidation (i.e.…”

Synthesis and circular dichroism of some bicyclic compounds related to camphor with chirality due to deuterium substitution

“…136 "C (lit.,'m.p. 137.5-139 "C) m/e 153 (M) (34% 'H); h([0])(cyclohexane) 487 (69), 465 (59,447 (28), 432 (17), 420 (9), 330 (9), 3 15 (3 I), 330 (55), 286 (60), 274 (44), 263 (I 8), and 253 nm (5).…”

“…and (1 b). These compounds were used as substrates in the synthesis of the models (Z), (3), 17 An alternative, more efficient and very simple route was also proposed for the synthesis of the key intermediate (2a) (Scheme). This procedure is also based on (+)-ketopinic acid (9, which was transformed into the a-diketone (9) by the action of selenium dioxide in acetic acid.…”