- Connective synthesis of spirovetivanes: Total synthesis of (±)-agarospirol, (±)-hinesol and (±)-α-vetispirene
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A concise, connective synthesis of naturally occurring spirovetivanes 1 and 3, in racemic form, is presented. This novel approach involves the efficient assembly of the advanced intermediate 12 through a unique spiroannulation protocol. Wiley-VCH Verlag GmbH & Co. KGaA1 69451 Weinheim, Germany, 2004.
- Maulide, Nuno,Vanherck, Jean-Christophe,Marko, Istvan E.
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p. 3962 - 3967
(2007/10/03)
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- A NOVEL SKELETAL REARRANGEMENT OF BICYCLO(2.2.2)OCTENES THROUGH BICYCLO(3.2.1)OCTENE SYSTEM: SYNTHESIS OF (+/-)-HINESOL AND (+/-)-10-epi-HINESOL
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Acid catalysed rearrangement of the endo-alcohol (9) leads to the ketones (11) and (12) having the bicyclo(3.2.1) and bicyclo(2.2.2) moieties.An efficient entry into spiro(4,5)decane and eremane system, as exemplified by the total synthesis of (+/-)-hinesol (2) and its 10-epimer (3) is reported.
- Rao, G.S.R. Subba,Janaki, Seenivasaga N.
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p. 3105 - 3108
(2007/10/02)
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- A New Synthesis of (+/-)-Agarospirol and (+/-)-Hinesol
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(+/-)-Agarospirol (8) and (+/-)-hinesol (9) were simultaneously synthesized via a useful synthon in the synthesis of spirovetivane-type sesquiterpenes, i.e., (2S*,5S*,10R*)-2-hydroxy-6,10-dimethylspirodec-6-en-8-one (1), which had previously been prepared from the corresponding phenolic α-diazoketone via the spiro-annelation reaction and subsequent stereo-controlled Birch reduction, both reported in our previous communications.Keywords-(+/-)-agarospirol; (+/-)-hinesol; spirovetivane-type sesquiterpenes; useful synthon; (2S*,5S*,10R*)-2-hydroxy-6,10-dimethylspirodec-6-en-8-one
- Iwata, Chuzo,Ida, Yasuo,Miyashita, Kazuyuki,Nakanishi, Tsutomu,Yamada, Minoru
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p. 2738 - 2741
(2007/10/02)
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