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. 2000 Nov 8;122(44):11027-11028.
doi: 10.1021/ja0027416. Epub 2000 Oct 21.

Total Synthesis of (-)-Laulimalide

Arun K Ghosh  1 , Yong Wang  1
Affiliations

Total Synthesis of (-)-Laulimalide

Arun K Ghosh et al. J Am Chem Soc. .
No abstract available

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Figures

Figure 1.
Figure 1.
Scheme 1<sup>a</sup>
Scheme 1a
a (a) Dibal-H, −78 °C then CSA, EtOH, 23 °C; (b) K-10, CH2 = CHOTBS, 23 °C; (c) NaBH4, MeOH, 0 °C (54%); (d) TBSCl, imidazole, DMF, 23 °C (75%); (e) Li, NH3 (95%); (f) I2, PPh3, Imidazole (96%); (g) 8, NaH, DMF, 0°C then iodide 7, 60 °C (89%); (h) Red-Al, THF, 0 °C; (i) PhCOCl, Et3N, DMAP (cat.); (j) Na(Hg), Na2HPO4, MeOH, −20° to 23 °C (72%); (k) MOMCl, i-Pr2NEt, 23 °C; (l) DDQ, pH 7 buffer, 23 °C (81%); (m) DMSO, (COCl)2, i-Pr2NEt, −60 °C (85%).
Scheme 2<sup>a</sup>
Scheme 2a
a (a) n-BuLi, −78 °C, 1 h and 23 °C, 1 h then 13, −78 °C (64%); (b) Dess−Martin, CH2Cl2, 23 °C (81%); (c) L-Selectride, THF, −78 °C (87%); (d) Red-Al, THF, −20 °C (81%); (e) CF3CO2H, CH2Cl2, 23 °C; (f) p-MeO-Ph-CH(OMe)2, CSA, CH2Cl2, 23 °C (71%); (g) Dibal-H, CH2Cl2, −78 °C (74%).
Scheme 3<sup>a</sup>
Scheme 3a
a (a) n-BuLi, −78°C, 15 min, Then 2, −78 to −40 °C, 2 h; (b) Ac2O, Et3N, DMAP (cat.); (c) Na(Hg), Na2HPO4, MeOH, −20 to 23 °C (34%); (d) (CF3CH2O)2P(O)CH2CO2H, Cl3C6H2COCl, i-Pr2NEt, DMAP; (e) AcOH-THF-H2O (3:1:1), 23 °C (99%); (f) Dess−Martin, CH2Cl2, 23 °C (79%); (g) K2CO3, 18-C-6, −20 to 0 °C (84%); (h) hv, Et2O, 50 min (66%); (i) PPTS, t-BuOH, 84 °C (45%) (j) Ti(OiPr)4, (+)-DET, t-BuOOH, −20 °C; (k) DDQ, pH 7, 23 °C (48%).
See this image and copyright information in PMC

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