Stereoselective synthesis (+)-cephalosporolide D

Reddy, G. Venkateswar; Kumar, R. Sateesh Chandra; Sreedhar, Eppakayala; Babu, K. Suresh; Rao, J. Madhusudana

doi:10.1016/j.tetlet.2010.01.082

Cited by 26 publications

(8 citation statements)

References 26 publications

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“…In order to determine the absolute configuration of dothiorelone A, a cross metathesis with chiral olefin 19 was also performed, giving 20 (Scheme ). Reduction of 20 under the same conditions that were used for 17 caused a partial cleavage of an allylic benzyl ether moiety.…”

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confidence: 99%

Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring

et al. 2011

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Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.

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confidence: 99%

Synthesis and Structural Revision of Phomopsin B, a Novel Polyketide Carrying a 10-Membered Cyclic-Ether Ring

et al. 2011

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“…[13] Oxidation of the formed primary alcohol under Swern conditions afforded desired aldehyde 4. Marouka allylation [4,14] of 4 by using titanium complex (S,S)-I and allyltri-n-butyltin yielded key fragment 3 with excellent enantioselectivity of 98 % ee (determined by chiral HPLC) in 86 % yield. With required fragment 3 in hand, we proceeded with the synthesis of topsentolide B 3 (Scheme 3).…”

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confidence: 99%

The First Total Synthesis of Topsentolide B₃

et al. 2011

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“…It involved the reaction of acid 183 in the presence of N,N-diisopropylethylamine (DIPEA), 2,4,6-trichlorobenzoyl chloride and DMAP in benzene for the construction of the macrolactone 184 and subsequent removal of the protecting group in acid conditions (Scheme 24). 159 A series of eight-membered lactones 188 were accomplished via [6 + 2] cyclization reaction of (1,6)-amphoteric systems, 2-(oxetan-3-yl)arylaldehydes 186, with siloxy alkynes 187 mediated by triflimide (HNTf 2 ) in dichloromethane at room temperature (Scheme 25). 160 Oxidative lactonization of 1,7-diol 189 carried out in the presence of a catalytic amount of TEMPO and PhI(OAc) 2 afforded eight-membered lactone 190.…”

Section: Lactonizationmentioning

confidence: 99%