Stereoselective syntheses of siphonarienal and siphonarienone

Ghanty, Supriya; Kumar, Chinta Krinda Suresh; Reddy, B. V. Subba

doi:10.1016/j.tetasy.2015.07.001

Cited by 4 publications

(3 citation statements)

References 36 publications

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“…4H), 1.06 (s, 9H), 0.91 (d, J = 6.6 Hz, 3H), 0.86 (d, J = 6.6 Hz, 3H), 0.81 (d, J = 6.3 Hz, 3H); 13 C NMR (CDCl 3 , 75 MHz) δ 135.8, 134. 3, 129.6, 127.7, 69.5, 69.2, 41.8, 41.5, 33.3, 33.3, 27.3, 27.0, 19.5, 19.4, 17.0, 16.5 (2R,4s,6S)-2,4,6-Trimethylheptane-1,7-diyl Bis(4-bromobenzoate) (22). To an ice-cold solution of the above primary alcohol 21 (90 mg, 0.218 mmol, 1.0 equiv) in anhydrous THF (3 mL) under argon was added TBAF (0.33 mL, 0.33 mmol, 1 M solution in THF, 1.5 equiv) over 2 min.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…This was hydrogenated further to give compound 19 as a colorless liquid. Comparison of the spectroscopic data of compound 19 with those of its known C-4 epimeric compound 22 revealed that there are considerable mismatches (please see Table S2 in the Supporting Information). This clearly indicated that the α- chiral methyl center of aldehyde 17 did not epimerize during the Swern oxidation or in the subsequent base-catalyzed HWE reaction.…”

Section: ■ Introductionmentioning

confidence: 99%

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Total Synthesis of Reported Structure of Baulamycin A and Its Congeners

et al. 2017

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A convergent and flexible strategy for the stereoselective total synthesis of the reported structure of baulamycin A and its congeners has been developed for the first time. Synthetic highlights include a Crimmins aldol reaction to construct the C-1' and C-14 centers, a Crimmins acetate aldol reaction to generate the hydroxy group at the C-13 position, Horner-Wadsworth-Emmons olefination to form the C-C bond, and Evans methylation to install the C-8 center. This synthetic study disclosed that the reported structure of baulamycin A needs to be revised, as its spectroscopic data are not identical with those of the synthetic baulamycin A.

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Section: ■ Conclusionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Total Synthesis of Reported Structure of Baulamycin A and Its Congeners

et al. 2017

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“…Adapted from Kakeya et al 63 Another route for the synthesis of siphonarienal (1) and siphonarienone (2) starting from Roche ester 130 was reported by Reddy. 64 Conversion of 130 in six steps into mono-TBDPS protected diol 114 employing kinetic resolution with a commercially available glucose oxidase from Aspergillus niger as the key step, and subsequent reactions via the ethyl ester analogue of 120 as described in Scheme 15 gave target compounds 1 and 2, respectively.…”

Section: Ex Chiral Pool Synthesis From the Roche Estermentioning

confidence: 99%

Strategies for the Synthesis of Deoxypropionates

Schmid

Baro

2016

Synthesis

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Deoxypropionates constitute an important class of polyketide natural products. The biological properties of deoxypropionates are diverse and synthetic strategies toward their preparation are equally manifold. This short review presents some recent developments on the synthesis of deoxypropionate units involving, besides iterative and noniterative routes, other methods such as stereoselective Mukaiyama reactions or lithiation-borylation-protodeboronation sequences.

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Herstellung enantiomerenangereicherter sekundärer Alkyllithium‐ und Alkylkupferverbindungen – Synthese von (−)‐Lardolure und Siphonarienal

et al. 2018

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Enantiomerenangereicherte sekundäre Alkyliodide wurden in sekundäre Alkyllithium‐ und Alkylkupferverbindungen unter hoher Retention der Konfiguration überführt. Abfangreaktionen mit unterschiedlichen Elektrophilen, einschließlich chiraler Epoxide, lieferten eine Bandbreite von chiralen Molekülen mit hoher Enantiomerenreinheit (>90 % ee). Diese Methode wurde, ausgehend von kommerziell erhältlichem Ethyl‐(R)‐3‐hydroxybutyrat (>99 % ee), in einer iterativen Weise für die Totalsynthese von (−)‐Lardolure in 13 Stufen und 5.4 % Gesamtausbeute (>99 % ee, dr>99:1) und Siphonarienal in 15 Stufen und 5.6 % Gesamtausbeute (>99 % ee, dr>99:1) angewendet.

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Stereoselective syntheses of siphonarienal and siphonarienone

Cited by 4 publications

References 36 publications

Total Synthesis of Reported Structure of Baulamycin A and Its Congeners

Total Synthesis of Reported Structure of Baulamycin A and Its Congeners

Strategies for the Synthesis of Deoxypropionates

Herstellung enantiomerenangereicherter sekundärer Alkyllithium‐ und Alkylkupferverbindungen – Synthese von (−)‐Lardolure und Siphonarienal

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