An effective practical method for the synthesis of chiral propargyl alcohols

Yadav, J. S.; Deshpande, P. K.; Sharma, G. V. M.

doi:10.1016/s0040-4020(01)87888-1

Cited by 115 publications

(46 citation statements)

References 61 publications

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“…It should be noted, however, that the published synthesis of alkyne 132 involves a five-step linear sequence from commercially available starting materials and uses a Sharpless asymmetric epoxidation to secure the required stereochemistry. [191] The asymmetric approach to 1 and 2 taken by Braun and Bauer was to perform an asymmetric aldol addition onto the formyl derivative 89, [192] by using their asymmetric acetate enolate equivalents derived from (R)-and (S)-(2-hydroxy-1,2,2-triphenylethyl) acetate (Scheme 14). [193] While these reagents generally give very high stereocontrol, the selectivity Scheme 14.…”

Section: Asymmetric Approachesmentioning

confidence: 99%

The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products

Papageorgiou

Assimopoulou

Couladouros

et al. 1999

Angew. Chem. Int. Ed.

563

463

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Section: Asymmetric Approachesmentioning

confidence: 99%

The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products

Papageorgiou

Assimopoulou

Couladouros

et al. 1999

Angew. Chem. Int. Ed.

563

463

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“…The synthesis of acid component 130 began with 134 prepared from homopropargyl alcohol 133 by a literature procedure [155]. The primary hydroxyl group in 134 was oxidized with DMP to afford the corresponding aldehyde, which was further oxidized to the acid 130.…”

Section: Ten-membered Macrolides 10 and 11mentioning

confidence: 99%

“…The commercially available trans-2-hexenol 152 was subjected to Sharpless AE to give a chiral epoxy alcohol, which was converted to epoxy chloride and then treated following an earlier reported procedure [155] to produce chiral propargyl alcohol 153. The TBS ether of 153 was treated with n-BuLi followed by reaction with ethyl chloroformate to yield an , -unsaturated ester, which was subjected to cis reduction under Lindlar's conditions to give Z olefin 154.…”

Section: Stagonolides (17-21 44 45)mentioning

confidence: 99%

Nonanolides of Natural Origin: Structure, Synthesis, and Biological Activity

Sun¹,

Lu²,

Ree³

et al. 2012

curr med chem

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Naturally occurring nonanolides (synonym decanolides) are a large family of secondary metabolites with an interesting 10- membered macrolide subunit. Metabolites of the nonanolide family have been found to have various biological activities, including cytotoxic, phytotoxic, antimalarial, antifungal, antibacterial, and antimicrofilament activities. An early review of the chemistry and bioactivity of nonanolides was presented in 1996, covering the literature published between 1975 and 1995. During the past decades, the broad spectrum of bioactivity and the intriguing structure of the medium-sized ring in nonanolide analogues have continuously drawn the attention of biologists and natural product and synthetic chemists, resulting in a great number of publications. This review summarizes in whole the recent progress in the field of the nonanolides of natural origin, aiming to give the readers a brief view of the compounds, concerning their natural occurrence, structural elucidation, biological activities, total synthesis, and structure-activity relationships. The article covers the literature published in the period from the beginning of 1996 to July 2011.

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“…[ [191] Die von Braun und Bauer beschriebene asymmetrische Synthese von 1 und 2 beruht auf einer enantioselektiven Aldoladdition an den Aldehyd 89 [192] unter Verwendung des von ihnen entwickelten chiralen Acetatenoläquivalents 135, das aus (R)-bzw. (S)-(2-Hydroxy-1,2,2-triphenylethyl)acetat gebildet wird (Schema 14).…”

Section: Asymmetrische Synthesenunclassified