Issue in Honor of Prof Csaba Szantay ARKIVOC 2008 (iii) 80-90 ISSN 1551-7012 Page 80 © ARKAT USA, Inc. Bicyclo[2.2.2]octane analogues of patchouli alcohol by Sakurai reaction and Nagata cyclization. Synthesis and olfactory properties of novel isopropyl derivatives † Angela La Bella, a, b Ilaria Popolla, a, b Marco Felici, a, b Francesca Leonelli, a, b Francesca Ceccacci, a, b Luigi Filocamo, c Luisa Maria Migneco, a, b and Rinaldo Marini Bettolo a, b* a Istituto di Chimica Biomolecolare del CNR, Sezione di Roma, b Dipartimento di Chimica, c Dipartimento di Scienze Biochimiche “A. Rossi Fanelli” Università degli Studi di Roma “La Sapienza”, P.le Aldo Moro 5, I-00185 Roma, Italy E-mail: rinaldo.marinibettolo@uniroma1.it Dedicated to Prof. Csaba Szántay on his 80 th birthday Abstract The synthesis of bicyclo[2.2.2]octane patchouli alcohol analogues by the Sakurai conjugate addition and Nagata cyclization is described. By this approach, complementary to those so far adopted and based on the Diels-Alder addition, known analogues 2, 3 and 20 and new analogues 8-11, with 1-isopropylbicyclo[2.2.2]octane structure, could be obtained. The olfactory properties of 8 and 10 were also evaluated. Keywords: 1-isopropylbicyclo[2.2.2]octane derivatives, synthesis, Sakurai allylation, Nagata cyclization, patchouli alcohol analogues, olfactory properties Introduction The olfactory properties of patchouli alcohol 1, a sesquiterpenoid largely available from natural sources, are well known. Since total synthesis 2 has proven uneconomical, a systematic search for synthetic analogues with simpler structures I (R=H, alkyl, alkenyl) and II (R=H, alkyl, alkenyl) has been carried out by Spreitzer 3 and Weyerstahl. 4 † The work described in this paper constitutes part of the Ph.D. Thesis of A.L.B. 1