Synthesis and utilization of optically active 2-substituted 4-(trimethylsilyl)cyclopentanones: Synthesis of (−)-massoialactone and (+)-β-cuparenone

Asaoka, Morio; Hayashibe, S.; Sonoda, S.; Takei, Hisashi

doi:10.1016/s0040-4039(00)97727-x

Cited by 29 publications

(4 citation statements)

References 12 publications

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“…Bromination and desilylbromination gave the cyclopentenone 387, which was used in a synthesis of (+)-β-cuparenone (388,Scheme 87). 207 This method of ring contraction does actually show some stereoselectivity in the formation of the intermediate aldehyde. Thus the epoxide 389 gave a mixture (77:23) of the corresponding aldehydes, which could be reduced selectively at the aldehyde group to give the alcohol 390 with fair overall stereoselectivity.…”

Section: A Silyl Group To Create Chiralitymentioning

confidence: 96%

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Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

1997

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Section: A Silyl Group To Create Chiralitymentioning

confidence: 96%

“…Regioselective methylation gave the cyclopentanone 386 , with high selectivity (>91:9) for attack anti to the silyl group across the five-membered ring. Bromination and desilylbromination gave the cyclopentenone 387 , which was used in a synthesis of (+)-β-cuparenone ( 388 , Scheme ) 87 …”

Section: A Silyl Group To Create Chiralitymentioning

confidence: 99%

Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds

1997

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“…Another formal synthesis leading to 362 reported 3 years later begins with the silylated cyclopentanone 364 , obtained in three steps from enantiomerically pure cyclohexenone 363 (Scheme ). The following compound 365 was synthesized in six steps (29.6% OY) and transformed into the target bicyclic enone 362 in 51.8% OY through a four-step sequence involving cyclization.…”

Section: Synthesismentioning

confidence: 99%

Tricyclic Sesquiterpenes from Marine Origin

et al. 2017

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The structure elucidation, biosynthesis, and biological activity of marine carbotricyclic sesquiterpene compounds are reviewed from the pioneering results to the end of 2015. Their total syntheses with a particular emphasis on the first syntheses, enantiomeric versions, and syntheses that led to the revision of structures or stereochemistries are summarized. Overall, 284 tricyclic compounds are classified into fused, bridged, and miscellaneous structures based on 54 different skeletal types. Tricyclic sesquiterpenes constitute an important group of natural products. Their structural diversity and biological activities have generated further interest in the field of drug discovery research, although the exact mechanisms of action of these species are not well known. Furthermore, these tricyclic structures, according to their chemical complexity, are a source of inspiration for chemists in the field of total synthesis for the development of innovative methodologies.

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“…A number of procedures have been reported for the preparation of both natural (-)-(R)- [1,[3][4][5][6][7][8][9][10][11][21][22][23][24][25][26][27][28][29][30] and synthetic (+)-(S)-massoia lactone [1, 21, 23-25, 28, 31], but the use of these procedures is restricted because of expensive reagents [7,14,26], low selectivity [6,10,11,22,25], enzymatic transformations [1,9,16,24], and large number of steps [3,27,29]. The present article describes a stereoselective synthesis of (-)-(6R)-massoia lactone with the use of methyl 3-[(tributylstannyl)methyl]but-3-enoate (V) as C 5 -allylic building block, which is available from ethyl 3,3-diethoxypropionate (VI) in five preparative steps (Scheme 1) [32,33].…”

mentioning

confidence: 99%