121840-74-2

Upstream product

• 79265-79-5 (8S,10S,13R)-7,13-Dimethyl-1,4-dithia-dispiro[4.2.4.2]tetradec-6-en-10-ol 
• 79265-78-4 (2S^*,5S^*,10R^*)-2-hydroxy-6,10-dimethylspiro<4.5>dec-6-en-8-one 
• 51388-76-2 (2S^*,5S^*,10R^*)-6,10-dimethylspiro<4.5>dec-6-en-2-ol 
• 81346-19-2 (5S^*,10R^*)-3-chloro-6,10-dimethylspiro<4.5>deca-2,6-diene-2-carboxylic acid 
• 81346-18-1 (5S^*,10R^*)-3-chloro-6,10-dimethylspiro<4.5>deca-2,6-diene-2-carbaldehyde 
• 18444-84-3 (5S^*,10R^*)-6,10-dimethylspiro<4.5>dec-6-en-2-one 
• 186581-53-3 diazomethane 
• 81346-20-5 (2RS,5R^*,10R^*)-6,10-dimethylspiro<4.5>dec-6-ene-2-carboxylic acid 
• 121741-13-7 6-Hydroxy-6,10-dimethyl-spiro[4.5]decane-2-carboxylic acid methyl ester 
• 121741-12-6 6-Methyl-10-oxo-spiro[4.5]decane-2-carboxylic acid 
• 121741-18-2 6-Hydroxy-6,10-dimethyl-spiro[4.5]decane-2-carboxylic acid 
• 121840-75-3 6-Methyl-10-methylene-spiro[4.5]decane-2-carboxylic acid methyl ester 

Downstream Products

• 1460-73-7 (2RS,5SR,10SR)-hinesol 
• 1460-73-7 (+/-)-10-epi-hinesol 
• 1460-73-7 (±)-agarospirol 
• 59331-07-6 (+/-)-hinesol 
• 1460-73-7 2-[(3R,5R,6R)-6,10-dimethylspiro[4.5]dec-9-en-3-yl]propan-2-ol 

Relevant academic research and scientific papers

Connective synthesis of spirovetivanes: Total synthesis of (±)-agarospirol, (±)-hinesol and (±)-α-vetispirene

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.

A NOVEL SKELETAL REARRANGEMENT OF BICYCLO(2.2.2)OCTENES THROUGH BICYCLO(3.2.1)OCTENE SYSTEM: SYNTHESIS OF (+/-)-HINESOL AND (+/-)-10-epi-HINESOL

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.

A New Synthesis of (+/-)-Agarospirol and (+/-)-Hinesol

(+/-)-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