Total synthesis of dl-sirenin

Corey, E. J.; Achiwa, Kazuo; Katzenellenbogen, John A.

doi:10.1021/ja01043a068

Cited by 125 publications

(65 citation statements)

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“…We include adamantate in this study as a relevant comparative example. 2,4,6-Trimethylbenzoyl chloride (mesitoyl chloride) has been used to protect hydroxyl groups during multi-step syntheses either in the presence of pyridine or silver cyanide to form mesitoyl esters (Corey et al 1969;Takimoto et al 1976). The mesitoyl group is exceptionally stable even to basic alcoholysis or hydrolysis, and has been used as a protective group in the regioselective synthesis of 6-deoxy-6-fluorolactosides (Cai et al 1992).…”

Section: General Methodsmentioning

confidence: 99%

Studies on regioselective acylation of cellulose with bulky acid chlorides

Tate

et al. 2010

Cellulose

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The regioselective esterification of cellulose by reaction with bulky acyl halides including pivaloyl chloride, adamantoyl chloride and 2,4,6-trimethylbenzoyl chloride was studied. Functionalization conditions to achieve a given degree of substitution (DS) and the resulting ester substitution pattern were described in detail. One-and twodimensional NMR spectroscopy techniques were used to confirm the structure of the esters obtained. We compared the effects on substitution of using different esterifying reagents and solvent systems including DMAc/LiCl, DMSO/TBAF, and ionic liquids (ILs).

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Section: General Methodsmentioning

confidence: 99%

Studies on regioselective acylation of cellulose with bulky acid chlorides

Tate

et al. 2010

Cellulose

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“…In the addition of Me 2 CuLi reagents to electron-deficient acetylenes [85][86][87][88], DCDtype complexes have been identified by NMR [84,89]. As shown below, an ynoate affords a vinylcopper intermediate, while an ynone instead affords an allenolate (Eq.…”

Section: ð10:8þmentioning

confidence: 99%

Mechanisms of Copper‐mediated Addition and Substitution Reactions

Mori¹,

Nakamura²

2002

Modern Organocopper Chemistry

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“…9 and Oil of Cubeb, Extra, gave the known p-cubebene norkemass spectrum) of this material were identical tone, m.p. 60-60.5" (lit.…”

Section: Methodsmentioning

confidence: 62%

Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

Piers¹,

Britton²,

Waal³

1971

Can. J. Chem.

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An efficient total synthesis of the racemic forms of the novel tricyclic sesquiterpenes a-cubebene (1) and 8-cubebene (2) is described. The key step of this synthesis involved the cupric sulfate catalyzed intramolecular cyclization of the olefinic diazoketone 3, which produced, in high yield, (+)-8-cubebene norketone (24) and (f )-l,6-epi-p-cubebene norketone (25), in a ratio of approximately 3:5, respectively.

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Total synthesis of dl-sirenin

Cited by 125 publications

References 0 publications

Studies on regioselective acylation of cellulose with bulky acid chlorides

Studies on regioselective acylation of cellulose with bulky acid chlorides

Mechanisms of Copper‐mediated Addition and Substitution Reactions

Total Synthesis of ( ± )-α-Cubebene and ( ± )-β-Cubebene

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