Corrigendum to "Stereoselective total synthesis of (+)-cardiobutanolide and (+)-3-epi-cardiobutanolide from diacetone d-glucose". [Tetrahedron Lett. 47 (2006) 4627] (DOI:10.1016/j.tetlet.2006.04.146)

Full text of DOI:10.1016/j.tetlet.2006.06.093

Tetrahedron Letters 47 (2006) 6695
Corrigendum
Corrigendum to ‘‘Stereoselective total synthesis
of (+)-cardiobutanolide and (+)-3-epi-cardiobutanolide
from diacetone D-glucose’’
[Tetrahedron Lett. 47 (2006) 4627]
Palakodety Radha Krishna* and P. V. Narsimha Reddy
D-206/B, Discovery Laboratory, Organic Chemistry Division-III, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Available online 1 August 2006
The following errors are to be noted:
(1) Scheme 1, Page 2: The synthetic sequence starts with the major isomer 6, which is converted into the requisite
isomer 7 by a two-step sequence and not as mentioned (from 7). The same is described on Page 1, column 2,
paragraph 2, lines 8–17.
(2) Scheme 1. Reagents and conditions: (b) BnBr, NaG, THF, 0 °C–rt, 1 h (80%). Please note that it is NaH and not
as printed.
HO
Ph
HO
Ph
O
Ref. 8
O
O
D-glucose
O
+
O
BnO
O
BnO
6
7
BnO
Ph
OBn OBn
OBn OBn
O
a, b
O
e, f
c, d
6
Ph
OTBS
10
OBn OBn
Ph
OH
O
O
O
OH OH
BnO
8
9
OBn OBn
OH
O
OBn OBn OH
g
j
h, i
COOEt
Ph
OH
Ph
Ph
O
O
OH
O
O
O
11
5
4
OH OH
OH
O
k
Ph
OH
O
2
Scheme 1. Reagents and conditions: (a) (i) p-NO2–PhCOOH, DEAD, TPP, THF, 0 °C–rt, 6 h; (ii) K2CO3, MeOH, rt, 1 h, (85% over two steps); (b)
BnBr, NaH, THF, 0 °C–rt, 1 h (80%); (c) 30% aq AcOH, reflux, 6 h (70%); (d) LiAlH4, THF, 2 h, 0 °C–rt, (65%); (e) TBSCl, imidazole, CH2Cl2
(85%); (f) 2,20-DMP, PPTS, CH2Cl2, rt, (85%); (g) TBAF, THF, rt, (90%); (h) (COCl)2, DMSO, Et3N, CH2Cl2, ꢀ78 °C; (i) EtOAc, LiHMDS, THF,
ꢀ78 °C, 1 h (60% over two steps); (j) 80% aq, AcOH, 6 h; (70%); (k) 10% Pd–C/H2, MeOH, (80%).
DOI of original article: 10.1016/j.tetlet.2006.04.146
*
Corresponding author. Tel.: +33 320964379; fax: +33 320964906; e-mail: prkgenius@iict.ap.nic.in
0040-4039/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved.
doi:10.1016/j.tetlet.2006.06.093