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1 article(s) from Ramakrishna, Sayini

Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

Pamarthi Gangadhar,
Sayini Ramakrishna,
Ponneri Venkateswarlu and
Pabbaraja Srihari

Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206

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Figure 1: Proposed structures of a selection of diacetylenic polyol natural products.

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Scheme 1: Retrosynthesis of strongylodiols H and I.

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Scheme 2: Synthesis of alkyne 19 and iodo intermediate 21. Reagents and conditions: (a) n-BuLi, THF, −78 °C t...

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Scheme 3: Stereoselective synthesis of (R)-25. Reagents and conditions: (a) CuCl, NH₂OH·HCl, 30% n-BuNH₂, Et₂...

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Figure 2: Absolute configuration analysis of alcohol 25. ∆δ = δ_S − δ_R for the (R)- and (S)-MTPA ester of alco...

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Scheme 4: Synthesis of strongylodiol H (9). Reagents and conditions: (a) TBDPSCl, imidazole, CH₂Cl₂, 0 °C to ...

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Figure 3: Previously proposed and revised structure of strongylodiol H (9).

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Scheme 5: Synthesis of compound 25a. Reagents and conditions: (a) (R)-CBS catalyst, BH₃·DMS, −50 °C, 16 h, 86...

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Scheme 6: Synthesis of strongylodiol I (10a). Reagents and conditions: (a) (i) TBDPSCl, imidazole, CH₂Cl₂, 0 ...

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Published 04 Sep 2018

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