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10 Crystal structure analysis of 11: data collection: KappaCCD dif-
fractometer. Cell refinement: HKL Scalepack (Otwinowshi & Minor
1997). Data reduction: Denzo Scalepak (Otwinoowski & Minor,
1997). Program used to solve structure, SIR92 (Altomare et al.,
1994). Program used to refine structure: CRYSTALS (Watkin et. al.,
2001). T = 200 K, MoKα radiation, λ = 0.710373 Å, structure
presentation: crystal dimensions 0.60 × 0.56 × 0.50 mm3, colorless
prism, space group P21/a monoclinic, a = 12.9389 (2), b = 11.7515
(3), c = 16.9570 (4) Å, β = 111.054 (9)Њ, V = 2406.20 (9) Å3, Z = 4, Dx
= 1.200 Mg mϪ3, θ = 3.08–27.45Њ µ = 0.123 mmϪ1, 64739 measured,
5633 independent reflections, 3445 reflections with I > 3.00σ(I ), Rint
= 0.064, R = 0.035, wR = 0.041, S = 1.053, (∆/σ)max = 0.0006, ∆ρmin
=
Ϫ0.23, ∆ρmax = 0.21 e ÅϪ3. CCDC reference number 199385. See
data in .cif or other electronic format.
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(b) J. R. Luly and H. J. Rapaport, J. Org. Chem., 1981, 46, 2745.
12 The er was determined using chiral HPLC, this involved the syn-
thesis of racemic 17 using ethyl p-toluenesulfinate in place of 13 in
Scheme 4 (see ESI for details†).
13 A single crystal X-ray diffraction experiment was undertaken for 17.
The initial structure solution and refinement clearly revealed the
regiochemistry of the product, however, complex multi-site disorder
of the TBS group led to abandonment of a full refinement of the
structure (see ESI for an anisotropic displacement ellipsoid plot of
17 and unit cell dimensions†).
6 This DA–E–IMDA sequence is similar to the “pincer” Diels–Alder
reaction, which consists of two Diels–Alder reactions upon the same
alkyne see: ref 4b and M. Lautens and E. Fillion, J. Org. Chem.,
1997, 62, 4418–4427 and references cited therein.
7 For reviews on diversity-orientated synthesis using natural product-
like templates see: (a) P. Arya, R. Joseph and D. T. H. Chou, Chem.
Biol., 2002, 9, 145–156 and references cited therein; (b) D. G. Hall,
O r g . B i o m o l . C h e m . , 2 0 0 3 , 1, 1 8 4 2 – 1 8 4 4
1844