Synthesis of Punctatin A

Structure of Punctatin A

C15H24O3

Principal investigator	Leo A. Paquette
Publication year	1986
Synthesis type	Total
Number of steps	19 (linear)
References	J. Am. Chem. Soc. 1986, 108, 3841. J. Am. Chem. Soc. 1987, 109, 3017.

Part 1 of 1

intermediate structure

Li(Ot-Bu)3AlH

THF

0 °C, 9 min, 91%

intermediate structure

TMS(CH2)2OCH2Cl, i-Pr2NEt

CH2Cl2

RT, 4 h, 96%

intermediate structure

NaH
i-BuI

DMSO

RT to 65 °C, 5.5 h, 43% (54% BRSM)

intermediate structure

LiAlH4

Et2O

-78 to -30 °C, 30 min, 97%

intermediate structure

KH, n-Bu3SnCH2I

THF

RT, 3.5 h, 95%

See the Williamson Ether Synthesis

intermediate structure

n-BuLi

Hexane(s)

-78 °C to RT, 24 h, 34 %

See the Wittig Rearrangement-[2,3]

intermediate structure

i-Pr2NEt, MeOCH2Cl

CH2Cl2

RT, 20 min, 100%

intermediate structure

BH3.THF
H2O2 , H2O , NaOH

THF, Diglyme

RT to 50 °C, 25 h, 62%

intermediate structure

HCrO3Cl.Pyr

CH2Cl2

RT, 2.5 h, 100%

intermediate structure

NaOMe

MeOH

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

intermediate structure

hv

PhH

RT, 9.5 h, 37% (50% BRSM)

See the Norrish Reaction

intermediate structure

n-Bu4N+ F-

Diglyme

55 °C, 36 h, 81%

intermediate structure

HCrO3Cl.Pyr

CH2Cl2

RT, 60 min, 81%

intermediate structure

n-Bu4N+ F-, TMSCH2CO2Me

THF

RT, 30 min

intermediate structure

Pd(OAc)2

MeCN

RT, 33.5 h, 80% (2 steps)

See the Saegusa-Ito Oxidation

intermediate structure

NaBH4, CeCl3.7H2O

MeOH

0 °C, 20 min, 97%

See the Luche Reduction

intermediate structure

DEAD, Ph3P, BzOH

PhH

RT, 3 h, 62%

See the Mitsunobu Reaction

intermediate structure

HClO4

H2O, THF

RT, 25 h, 61% (73% BRSM)

intermediate structure

KOH

EtOH, H2O

50 °C, 3 h, 77%

intermediate structure

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