Synthesis and Structure Revision of Musclides-A2 and -B

Tezuka, Yasuhiro; Kudoh, Michiko; Hatanaka, Y.; Kadota, Shigetoshi; Kikuchi, Tohru

doi:10.1080/10575639708043643

Cited by 5 publications

(4 citation statements)

References 12 publications

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“…These were formed by the partial reductions of adducts 81 and 82 to the Z-alkenes, using Lindlar catalysis. The efficient transformation of the fully hydrogenated derivatives of 81 and 82, to musclide A1, has previously been reported [58].…”

Section: Scheme 21mentioning

confidence: 95%

Asymmetric Alkynylation Reactions of Aldehydes Using a Zn(OTf)2-Chiral Ligand-Base System

Tyrrell¹

2009

COC

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Optically active propargylic alcohols serve as an important building block in asymmetric synthesis. The customised synthesis of chiral ligands and transition metal activators as catalysts, to effect asymmetric alkynylation reactions, continue to feature in the literature. This review article focuses upon the use of Zn(OTf) 2 , in conjunction with 2-point chiral ligands, for effecting asymmetric alkynylation reactions to aldehydes.

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Section: Scheme 21mentioning

confidence: 95%

Asymmetric Alkynylation Reactions of Aldehydes Using a Zn(OTf)2-Chiral Ligand-Base System

Tyrrell¹

2009

COC

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“…16 Subsequent PtO 2 -catalyzed hydrogenation and sulfonation with sulfur trioxide-pyridine complex generated the sulfate 7 (66% yield over two steps). 17,18 Finally, debenzylation by Pd/C and hydrogen gave (2R,5R)-musclide-A1 in 81% yield and dr = 16:1 (based on an analysis of 1 H NMR data). 19 The specific rotation and NMR spectra of our synthetic musclide-A1 matched the literature values.…”

Section: Letter Syn Lettmentioning

confidence: 99%

“…17,18 Finally, debenzylation by Pd/C and hydrogen gave (2R,5R)-musclide-A1 in 81% yield and dr = 16:1 (based on an analysis of 1 H NMR data). 19 The specific rotation and NMR spectra of our synthetic musclide-A1 matched the literature values. 17 Scheme 4 Synthesis of (2R,5R)-musclide-A1…”

Section: Letter Syn Lettmentioning

confidence: 99%

“…[α]D 21 = -7.3 (c 0.7, CHCl3). 1 H NMR (300 MHz,CD3OD) δ 7.37 [20] To a stirred suspension of Pd/C (20.0 mg) in M eOH (1 mL) under H2 atmospher maintained at room temperature, a solution of 7 (0.100 g, 0.31 mmol, 1eq) in M eOH (3 mL) was added. The reaction was stirred for additional 8 h and monitored by TLC (SiO2, DCM /M eOH 10:1).…”

Section: (S)-4-(4-chlorophenyl)-4-hydroxybut-2-yn-1-yl Acetate (3k) (New Compound)mentioning

confidence: 99%

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Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst

Zhou

Wang

et al. 2019

Synlett

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A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93% yield; 95% ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2R,5R)-musclide-A1, a cardiotonic potentiating principle from musk.

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Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B

Amador

Ariza

García

et al. 2002

Tetrahedron Letters

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Synthesis and Structure Revision of Musclides-A2 and -B

Cited by 5 publications

References 12 publications

Asymmetric Alkynylation Reactions of Aldehydes Using a Zn(OTf)2-Chiral Ligand-Base System

Asymmetric Alkynylation Reactions of Aldehydes Using a Zn(OTf)2-Chiral Ligand-Base System

Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst

Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B

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