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Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206
Graphical Abstract
Figure 1: Proposed structures of a selection of diacetylenic polyol natural products.
Scheme 1: Retrosynthesis of strongylodiols H and I.
Scheme 2: Synthesis of alkyne 19 and iodo intermediate 21. Reagents and conditions: (a) n-BuLi, THF, −78 °C t...
Scheme 3: Stereoselective synthesis of (R)-25. Reagents and conditions: (a) CuCl, NH2OH·HCl, 30% n-BuNH2, Et2...
Figure 2: Absolute configuration analysis of alcohol 25. ∆δ = δS − δR for the (R)- and (S)-MTPA ester of alco...
Scheme 4: Synthesis of strongylodiol H (9). Reagents and conditions: (a) TBDPSCl, imidazole, CH2Cl2, 0 °C to ...
Figure 3: Previously proposed and revised structure of strongylodiol H (9).
Scheme 5: Synthesis of compound 25a. Reagents and conditions: (a) (R)-CBS catalyst, BH3·DMS, −50 °C, 16 h, 86...
Scheme 6: Synthesis of strongylodiol I (10a). Reagents and conditions: (a) (i) TBDPSCl, imidazole, CH2Cl2, 0 ...
Beilstein J. Org. Chem. 2014, 10, 3122–3126, doi:10.3762/bjoc.10.329
Figure 1: Structures of aspergillides.
Scheme 1: Retrosynthetic analysis for (−)-aspergillide C.
Scheme 2: Synthesis of 11. Reaction conditions: (a) n-BuLi, THF/HMPA (5:1), −78 °C to rt, 12 h, 95%; (b) Li, t...
Figure 2: Key NOESY correlations observed in compound 11.
Scheme 3: Synthesis of 4 and formal total synthesis of (−)-aspergillide C (3). Reaction conditions: (a) [Cp*(...