Structure of endo-(5R*,6R*,11R*,12S*)-5,6,11,12-tetrahydro-4,11,12-trimethoxy-9,13,13-trimethyl-5-(triethylsiloxy)-6,10-methano-8(7H)benzocyclodecenone

Sakai, Yoshitaka; Kojima, Yoshitaka; Ohashi, Yuji; Morihira, Koichiro; Furukawa, T.; Horiguchi, Yoshiaki; Kuwajima, Isao

doi:10.1107/s0108270191007916

Cited by 2 publications

(1 citation statement)

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“…Each was led to the cyclization precursor and, after protection of C2-OH with a silyl group, the cyclization reaction was examined in each case. By treatment with TiCl 4 , dienol silyl ether 2e of the Cram-type adduct afforded the corresponding 2b,9a,10a-endo tricarbocycle 3e, 24,25 whereas an exo tricarbocycle 3f-I 26 was obtained as a major product from 2f derived from the anti-Cram adduct.…”

Section: Equationmentioning

confidence: 99%

ChemInform Abstract: Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)‐Taxusin and (‐)‐Taxol

Kuwajima

Kusama

2000

ChemInform

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To construct taxane ABC tricarbocycles, a useful methodology including an aldol-like eight-membered B ring cyclization between dienol silyl ethers and acetals was explored. By applying this methodology, the enantioselective total syntheses of (+)-taxusin and (-) -taxol have been achieved, starting from the substrate containing a chiral center at each C1 site, based on AC to ABC strategies. Syntheses of several artificial taxoids are also described. 4Enantioselective Total Synthesis of (-)-Taxol 4.1 Synthetic Plan 4.2 Enantioselective Synthesis of the A-ring fragment 4.3 From A to AC and to ABC Tricarbocycles 4.4 Introduction of the C19 Methyl Group 4.5 Functional Group Manipulation for Total Synthesis of (-)-Taxol 5 Synthesis of Taxane Analogs 6 Conclusion

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Section: Equationmentioning

confidence: 99%

ChemInform Abstract: Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)‐Taxusin and (‐)‐Taxol

Kuwajima

Kusama

2000

ChemInform

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Synthesis of C-Aromatic Taxinine Derivatives

Seto¹,

Morihira²,

Katagiri³

et al. 1993

Chemistry Letters

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An oxygenated substituent at the 2-position (taxane numbering) plays a critical role to determine the endo/exo cyclization into the 8-membered ring system involved in the taxane skeleton, and the aromatic taxinine derivative was prepared from the corresponding 2α,9β,10α–exo cyclized compound through thermal exo-to-endo isomerization and a Lewis acid induced inversion on the C-9 and C-10 sites.

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Structure of endo-(5R,6R,11R,12S)-5,6,11,12-tetrahydro-4,11,12-trimethoxy-9,13,13-trimethyl-5-(triethylsiloxy)-6,10-methano-8(7H)benzocyclodecenone

Cited by 2 publications

References 1 publication

ChemInform Abstract: Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)‐Taxusin and (‐)‐Taxol

ChemInform Abstract: Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)‐Taxusin and (‐)‐Taxol

Synthesis of C-Aromatic Taxinine Derivatives

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