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. 2006 Dec 11;45(48):8217-20.
doi: 10.1002/anie.200603321.

Polyol synthesis through hydrocarbon oxidation: de novo synthesis of L-galactose

Dustin J Covell  1 , Nicolaas A Vermeulen, Nathan A Labenz, M Christina White
Affiliations

Polyol synthesis through hydrocarbon oxidation: de novo synthesis of L-galactose

Dustin J Covell et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
A hydrocarbon oxidation strategy for the streamlined construction of polyols.
Scheme 2
Scheme 2
Chiral (E)-2-butene-1,4-diols as key intermediates in stereodivergent hexose syntheses.
Scheme 3
Scheme 3
Total synthesis of differentially protected L-galactose (−)-11 (see the Supporting Information for full experimental details). a) mCPBA, CH2Cl2, 0 °C→RT (74%); b) oligomeric (R,R)-[(salen)CoIII]-OTf (0.05 mol%), CH3CN; then 2-methoxypropene, p-TsOH·H2O (1 mol%), 0°C; c) CuBr (10 mol%), CH2=CHMgBr, THF, −40 °C; d) NaH, TBAI (10 mol%), DMF, 0°C, BnBr, 0°C→RT, (54%, 3 steps from 8, 99% ee); e) [Pd(CH3CN)4](BF4)2 (10 mol%), PhBQ (2 equiv), 5 (3 equiv), DIPEA (0.5 equiv), 4-& MS, DMSO/CH2Cl2 (3:1), 41 °C, 72h (71%, linear/branched >300:1, E/Z =97:3); f) K2OsO4·2H2O (1 mol%), (DHQD)2PHAL (5 mol%), K3Fe(CN)6, K2CO3, MeSO2NH2, tBuOH/H2O, 0 °C (96%, >20:1 d.r.); g) TBSOTf, 2,6-lutidine, CH2Cl2, 0°C→RT, (90%); h) DIBAL, CH2Cl2, −78 °C, (98%); i) (COCl)2, DMSO, NEt3, −65 °C, (90%), j) Zn(NO3)2·6H2O, CH3CN, 50 °C, (93%). DHQD =dihydroquinidine, DIBAL = diisobutylaluminum hydride, DMF =N,N-dimethylformamide, PHAL =phthalazine, TBAI =tetra-n-butylammonium iodide, TBS =tert-butyldimethylsilyl, Ts =toluene-4-sulfonyl.
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