Chiral synthesis of polyketide-derived natural products. 27. Stereoselective synthesis of erythronolide A via an extremely efficient macrolactonization by the modified Yamaguchi method

Hikota, Masataka; Tone, Hitoshi; Horita, Kiyoshi; Yonemitsu, Osamu

doi:10.1021/jo00288a004

Cited by 135 publications

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“…of DMAP (5.0 m m , r.t.)) gave rise to decomposed products, resulting from the DMAP‐induced cleavage of the ester linkage (Entry 4). [18] However, reducing the amount of DMAP to 0.2 equiv. gave salicylide 29 in high yield (Entry 5).…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of the Proposed Structure of Ardimerin, and Proposal for its Structural Revision

Nakayama

Tanzer

Kusumi

et al. 2016

Helvetica Chimica Acta

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We report the first total synthesis of the proposed structure of ardimerin, which was achieved in 14 steps starting from 2,3,4‐trimethoxybenzoic acid. The key steps include the β‐selective formation of the crucial C‐glycoside linkage and stepwise construction of the strained eight‐membered salicylide core. The synthesis revealed that the proposed structure 1 does not match the natural product. A proposal is made for reassigning the isolated natural product to the already known structure of bergenin. Interesting properties of the synthetic eight‐membered salicylides are documented, including their susceptibility toward nucleophilic ring opening and the bowl chirality.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of the Proposed Structure of Ardimerin, and Proposal for its Structural Revision

Nakayama

Tanzer

Kusumi

et al. 2016

Helvetica Chimica Acta

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“…Oxidation into the carboxylic acid 28 was carried out via the aldehyde and desilylation gave the hydroxy-acid 29. Lactonisation was then accomplished using the modified Yamaguchi procedure [10] to give the unsaturated eight-membered ring lactone 30 which was isolated essentially as a single diastereoisomer.…”

Section: Resultsmentioning

confidence: 99%

Remote stereocontrol using (E)-6-hydroxy-4-methylhex-2-enyl(tri-n-butyl)stannane

MacCormick

Thomas

2006

Journal of Organometallic Chemistry

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“…Unfortunately, none of the above reactions yielded the desired product, and the only products obtained were the activated acid derivates, namely the Yamaguchi mixed anhydride and the Corey active ester, respectively. Some modern variations of these methods [48] were also tried, but they failed to give the desired product too. The most common cyclization methods, using DCC or its water-soluble derivatives and analogues, gave as the only product 2-(2-hydroxy-1,1- (19) in 36% yield (Scheme 5).…”

Section: Other Lactonisation Methodsmentioning

confidence: 99%

An Unexpected Formation of a 14‐Membered Cyclodepsipeptide

Iliev

Linden

Heimgartner

2003

Helvetica Chimica Acta

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The treatment of diluted solutions of the hydroxy diamides 6a and 6b in toluene with HCl gas at 100°gave the dimeric, 14-membered cyclodepsipeptide 10 in up to 72% yield (Scheme 3). The same product was formed from the linear dimer of 6b, the depsipeptide 11, under the same conditions (cf. Scheme 4). All attempts to prepare the cyclic seven-membered monomer 9, starting with different precursors and using different lactonization methods failed, and 10 was the only product which was isolated (cf. Scheme 6). For example, the reaction of the ester 20 with NaH in toluene at 80°led exclusively to the cyclodimer 10. On the other hand, the base-catalyzed cyclization of the hydroxy diester 22, which is the 'O-analogue' of 20, yielded neither the seven-membered dilactone, nor the 14-membered tetralactone, but only the known trimer 23 and tetramer 24 of 2,2-dimethylpropano-3-lactone (cf. Scheme 7). 2The treatment of diluted solutions of the hydroxydiamides 6a and 6b in toluene with HCl gas at 100 o gave the dimeric, 14-membered cyclodepsipeptide 10 in up to 72% yield (Scheme 3).The same product was formed from the linear dimer of 6b, the depsipeptide 11, under the same conditions (Scheme 4). All attempts to prepare the cyclic 7-membered monomer 9, starting with different precursors and using different lactonization methods failed, and 10 was the only product which was formed (Scheme 6). For example, the reaction of the ester 20 with NaH in toluene at 80 o led exclusively to the cyclodimer 10. On the other hand, the base catalyzed cyclization of the hydroxydiester 22, which is the 'O-analogue' of 20, yielded neither the 7-membered dilactone, nor the 14-membered tetralactone, but only the known trimer 23 and tetramer 24 of 2,2-dimethylpropiolactone (Scheme 7).3

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Chiral synthesis of polyketide-derived natural products. 27. Stereoselective synthesis of erythronolide A via an extremely efficient macrolactonization by the modified Yamaguchi method

Cited by 135 publications

References 0 publications

Total Synthesis of the Proposed Structure of Ardimerin, and Proposal for its Structural Revision

Total Synthesis of the Proposed Structure of Ardimerin, and Proposal for its Structural Revision

Remote stereocontrol using (E)-6-hydroxy-4-methylhex-2-enyl(tri-n-butyl)stannane

An Unexpected Formation of a 14‐Membered Cyclodepsipeptide

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