First total synthesis of (−)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid

Zhang, Xianshu; Da, Shijun; Zhang, Chao-Xin; Xie, Zhenzhen; Li, Ying

doi:10.1016/j.tetlet.2005.11.053

Cited by 3 publications

(3 citation statements)

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“…Two Brown’s allylations were key steps of the synthesis to establish the right configuration at the two stereocenters of the molecule. The reactions led to the expected homoallyl alcohol derivatives in high yields and stereoselectivities (Scheme ) …”

Section: Synthesis Of Natural Productsmentioning

confidence: 99%

“…The reactions led to the expected homoallyl alcohol derivatives in high yields and stereoselectivities (Scheme 112). 263 Verbalactone is a natural antibiotic isolated from the roots of Verbascum undulatum Lam., 264 a biennial plant of the genus Verbascum that belongs to the family Scrophulariaceae. This natural product is a macrocyclic symmetrical dimer of lactone (3R,5R)-dihydroxy-5-decanolide.…”

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confidence: 99%

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Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

2013

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2.2. Chiral Imines and Imine Derivatives 2.2.1. Imines and Imine Derivatives from Chiral Carbonyl Compounds. Chiral α-oxysubstituted aldehydes were used by Kobayashi and co-workers in a three-component reaction with allylboropinacolate and ammonia in ethanol. The corresponding homoallylic primary amines were obtained with good to high syn diastereofacial selectivities (Scheme 5). 20 The precise reaction mechanism was unclear. Preformation of N-Scheme 3 Scheme 4 Scheme 5 Chemical Reviews Review dx.

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Section: Synthesis Of Natural Productsmentioning

confidence: 99%

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confidence: 99%

Diastereoselective Allylation of Carbonyl Compounds and Imines: Application to the Synthesis of Natural Products

2013

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“…Very recently, Li et al reported the first total synthesis of 1 in 11 steps using asymmetric allylboration by B-allyldiisopinocampheylborane and hydroboration-oxidation reactions as the key steps. [3] As part of our continuing interest towards asymmetric synthesis of naturally occurring compounds, [4] we have accomplished the total synthesis of (-)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid (1) from commercially available epichlorohydrin using Jacobsen's HKR, Sharpless asymmetric dihydroxylation and regioselective opening of epoxide and cyclic sulfate as the key steps.…”

Section: Introductionmentioning

confidence: 99%