Synthesis of Punctatin A

C15H24O3
Principal investigator | Leo A. Paquette |
---|---|
Publication year | 1986 |
Synthesis type | Total |
Number of steps | 19 (linear) |
References |
Part 1 of 1

Li(Ot-Bu)3AlH
THF
0 °C, 9 min, 91%

TMS(CH2)2OCH2Cl,
i-Pr2NEt
CH2Cl2
RT, 4 h, 96%

- NaH
- i-BuI
DMSO
RT to 65 °C, 5.5 h, 43% (54% BRSM)

LiAlH4
Et2O
-78 to -30 °C, 30 min, 97%



i-Pr2NEt,
MeOCH2Cl
CH2Cl2
RT, 20 min, 100%

- BH3.THF
- H2O2 , H2O , NaOH
THF, Diglyme
RT to 50 °C, 25 h, 62%

HCrO3Cl.Pyr
CH2Cl2
RT, 2.5 h, 100%

NaOMe
MeOH
Reflux, 9.5 h, 66% (100% BRSM)


n-Bu4N+ F-
Diglyme
55 °C, 36 h, 81%

HCrO3Cl.Pyr
CH2Cl2
RT, 60 min, 81%

n-Bu4N+ F-,
TMSCH2CO2Me
THF
RT, 30 min




HClO4
H2O, THF
RT, 25 h, 61% (73% BRSM)

KOH
EtOH, H2O
50 °C, 3 h, 77%
